Herbicidal oxabicycloalkane ethers

ABSTRACT

The present invention relates to novel bicyclo ether derivatives, to compositions containing them, and to their method of use especially to control the growth of undesired vegetation in rice.

RELATED APPLICATION

This application is a continuation-in-part of my copending application U.S. Ser. No. 07/197,181, filed May 23, 1988, now abandoned.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to novel bicyclo ether derivative compounds, to compositions containing these ether derivative compounds, and to methods of using these compounds or compositions to control the growth of undesired vegetation.

2. Description of Related Art

Vieira et al., Helvetica Chimica Acta, 65(6) (1982), pp. 1700-06, teach the preparation of the oxabicyclic cyanohydrin acetates via a Diels-Alder reaction. ##STR1##

Vieria et al., Helvetica Chimica Acta, 66(6) (1983), pp. 1865-71 teach a chiral variant of the above described reaction which produces oxabicyclic cyanohydrin esters homologous to those depicted above, but with a (-)-camphanoyl group instead of an acetate group.

Black et al., Helvetica Chimica Acta, 67 (1984), pp. 1612-15, disclose a method for the preparation of the chiral oxabicyclic ketone via diastereoselective formation of a brucine complex of the corresponding cyanohydrin acetate. ##STR2##

Payne et al., U.S. Pat. No. 4,567,283 and Payne et al., U.S. Pat. No. 4,670,041 disclose a variety of herbicidal bicyclic ethers of the Formula ##STR3## wherein W is an unsaturated, aromatic or heterocyclic group. This reference also disclosed certain bicyclic and monocyclic intermediates to these compounds.

Payne et al., U.S. Pat. No. 4,525,203, disclose herbicidal bicyclic ethers of the Formula ##STR4##

GB 2188-931 discloses compounds of the following formula as herbicides: ##STR5##

SUMMARY OF THE INVENTION

This invention pertains to compounds of Formula I including stereoisomers, suitable agricultural compositions containing them and their use as broad spectrum preemergent and postemergent herbicides. ##STR6## wherein: X is (CH₂)_(m) ;

Y is (CR₃ R₄)_(p) ;

Z is (CR₃ R₄)_(n) ;

p is 0 to 2;

m is 0 to 2;

n is 1 to 3;

R₁ is H or a straight-chain C₁ -C₃ alkyl;

R₂ is H, C₁ -C₆ alkyl, C₂ -C₄ alkenyl, C₂ -C₄ alkynyl, phenyl or C₁ -C₄ alkyl substituted by halogen, Ph, OH, CN, OR_(a), SO₂ R_(a), PhSO₂, N₃, CO₂ R_(a), or CO₂ H;

R₃ is H or C₁ -C₃ alkyl;

R₄ is H or CH₃ ;

R₃ and R₄ may be taken together to form a 5- or 6-membered carbocyclic ring;

W is ##STR7## Z¹ is CH₂, NR₃, O, S or may be taken to form a double bond with an adjacent carbon;

R₅ is H, halogen, R_(a), OR_(a), SR_(a) or CN;

R₆ is H, F, Cl, CH₃, OCH₃, OH or OR_(a) ;

R_(a) is C₁ -C₃ alkyl;

q¹ is 0, 1 or 2; and

q is 0 to 2

provided that the sum of q and q¹ is 0, 1 or 2 and that if q and q¹ is O then Z¹ is CH₂.

Preferred for either their biological activity or ease of synthesis are:

1. Compounds of Formula I wherein;

R₂ is C₁ -C₃ alkyl, C₂ -C₃ alkenyl, C₂ -C₃ alkynyl, or C₁ -C₂ alkyl substituted by OH, CN, OCH₃, SO₂ CH₃, SO₂ Ph or CO₂ CH₃ ; and

R₅ is H, F, Cl, Br, CH₃, OCH₃, SCH₃ or CN.

2. Compounds of Preferred 1 wherein;

n is 2;

m is 1;

p is 0; and

R₃ is H or CH₃.

3. Compounds of Preferred 1 wherein;

n is 3;

m is 2;

p is 0; and

R₃ is H or CH₃.

4. Compounds of Preferred 1 wherein;

n is 1;

m is 2;

p is 1; and

R₃ is H or CH₃.

5. Compounds of Preferred 2, 3 or 4 wherein;

Z¹ is CH₂.

6. Compounds of Preferred 2, 3 or 4 wherein;

Z¹ is O.

7. Compounds of Preferred 2, 3 or 4 wherein;

Z¹ is S.

8. Compounds of Preferred 2, 3 or 4 wherein;

Z¹ is NR₃.

9. Compounds of Preferred 2, 3 or 4wherein;

W is ##STR8##

Specifically preferred are:

exo-2-(2,3-dihydro-1H-inden-1-yloxy)-1-methyl-4-(1-methylethyl)-7-oxabicyclo((2.2.1))heptane; and

exo-2-(2,3-dihydro-1H-inden-1-yloxy)-1,4-diethyl-7-oxabicyclo[2.2.1]heptane.

DETAILED DESCRIPTION OF THE INVENTION

The compounds of Formula I exhibit geometrical and optical isomerism and may be prepared in geometrically or optically pure or mixed forms. The various individual optical and geometrical forms and various combinations thereof of the materials of the invention usually have some difference in herbicidal properties. Generally preferred for herbicidal efficacy are 1) those geometrical isomers of Formula I wherein the OW group resides on the same face of the carbocyclic ring as the O-Y bridge and 2) those optical isomers with the absolute configuration depicted in Formula Ia. The present invention contemplates all of the herbicidally active forms resulting from synthesis and from deliberately created mixtures. ##STR9##

The compounds of Formula Ia may be synthesized according to the well known Williamson Ether Synthesis (see N. Baggett in Comprehensive Organic Chemistry, D. Barton and W. D. Ollis eds., Vol. 1, pp. 819-832, Pergamon Press, New York (1979)) as shown in Scheme I by allowing bicyclic alcohols of Formula IV to react with appropriate alkylating agents represented as W-L where W represents those organic radicals defined previously and LG represents leaving group moieties such as chloride, bromide, iodide, and sulfonate esters. This is outlined in Scheme I. ##STR10##

The bicyclic alcohols of Formula IV are known in the art (U.S. Pat. Nos. 4,670,041; 4,529,806; 4,486,219) and the alkylating agents W-LG are prepared in the conventional manners known to those skilled in the art from the alcohols W-OH.

The alcohols, WOH, are generally known in the art and are most conveniently prepared through metal hydride (e.g., sodium borohydride) reduction of the corresponding bicyclic ketones which can be derived by Friedel-Crafts type cyclization of derivatives of phenylalkylcarboxylic acid, phenoxyalkylcarboxylic acids, phenylthioalkylcarboxylic acids, benzyloxyalkylcarboxylic acids, and benzylthioalkylcarboxylic acids. Details may be found in a) T. Laird in Comprehensive Organic Chemistry, D. Barton and W. D. Ollis, eds., Vol. 1, pp. 1165-1168, Pergamon Press, New York (1979); b) M. H. Palmer and N. M. Scollick, J. Chem. Soc., C., (1968), 2833; c) C. E. Dalgliesch and Mann, J. Chem. Soc., (1945), 893; d) C. D. Hurd and S. Hayao, J. Am. Chem. Soc., (1954), 76, 4299 and 5056; and e) R. Lesser, Chem. Ber., (1923), 56, 1642.

Alternatively, the compounds of Formula Ia may be prepared by the coupling procedure described in Scheme II, which is used in cases where the standard Williamson ether synthesis proves problematic. This procedure uses a Lewis acidic metal oxide wherein the metal can remove the halide ion by forming an insoluble precipitate. In Example 1, silver (I) oxide is used and the silver halide is the co-product. Alternative metal oxides that may be used are HgO, CaO, MgO. N,N-Dimethylformamide and ethereal solvents, such as diethyl ether, tetrahydrofuran, dioxane, or 1,2-dimethoxyethane are the preferred solvents. Other solvents likely to provide good yields include dipolar aprotic solvents like dimethyl sulfoxide, acetone and N,N'-dimethylpropyleneurea. ##STR11##

The synthetic procedure shown in Scheme III may be used to prepare compounds of Formula Ia wherein Z₁ is a heteroatom (such as N, O, S). The coupling substrate is a styrene with an appropriate substituted heteroatom in protected form (such as with a trialkylsilyl, acetate ester, benzoate ester, etc.). A mild halogenating agent such as N-halosuccinimide, N-haloacetamide, dioxane dihalide, or pyridinium hydrohalide perhalide may be used to form a cyclic halonium ion under optional acid catalysis. The ion is intercepted at the benzylic center to form the benzylic ether. The heteroatom is deprotected and allowed to close in situ to form the desired heterocyclic ring. The acid catalyst for the initial coupling can be used in either concentrated or diluted form. ##STR12##

EXAMPLE 1 (±)-exo-2-(2,3-Dihydro-1H-inden-2-yl-oxy)-1-methyl-4-(1-methylethyl)-7-Oxabicyclo[2.2.1]heptane

(±)-Exo-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane-2-ol (2.51 g, 14.7 mmoles) was dissolved in 7.3 mL of diethyl ether in a one-neck flask. 1-chloroindane (3.37 g, 22.1 mmoles) was then added, followed by silver (I) oxide (Aldrich, 3.41 g, 16.2 mmoles). A reflux condenser was fitted to the flask and the reaction was heated at reflux for 12 hrs. The mixture was allowed to cool and filtered through a pad of Celite Florisil or SiO₂. The filter cake was washed with diethyl ether, the filtrate was concentrated and chromatographed on SiO₂ (10-20% Et₂ O/hexane) to obtain 2.12 g (51%) of the desired product as an oil in a 1:1 mixture of diastereomers.

¹ H-NMR (CDCl₃, 200 MHz): 7.40 (m, 1H); 7.23 (m, 3H); 4.95 (app.t, 1H); 3.75 (m, 1H); 3.10 (m, 1H); 2.80 (m, 1H); 2.50-2.00 (m, 4H); 2.80-2.40 (m, 8H); 1.05 (2d, 6H).

EXAMPLE 2 Exo-2-[2,3-dihydrobenzofuran-3-yl-oxy]-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane

2-ethenyl phenol was synthesized according to the procedure of Corson et al. (J. Org. Chem., 1958, 23, 544) and silated by standard procedures. 2-t-butyldimethylsiloxy styrene (550 mg, 2.03 mmoles) was dissolved in tetrahydrofuran (4.0 mL). Exo-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane-2-ol (690 mg, 4.06 mmoles) and N-bromosuccinimide were added. One drop of perchloric acid (70%) was added. The reaction was stirred for 11/2 hrs after which time a 1M solution of tetrabutylammonium fluoride in THF (2.5 mL) (any fluoride source, such as KF, NaF, CaF₂, HF will suffice) was added and the solution was stirred for an hour. The reaction mixture was diluted with diethyl ether and washed with H₂ O. The organic layer was dried over anhydrous Na₂ SO₄, filtered, and concentrated. It was then chromatographed on SiO₂ (10-20% Et₂ O/hexane) to obtain 210 mg of the desired product in about 95% purity.

¹ H-NMR (CDCl₃, 200 MHz): 7.30 (m, 1H); 7.25 (app. tdd, 1H); 6.90 (m, 2H); 5.10 (td, 1H); 4.85 (m, 2H); 3.70 (2dd, 1H); 2.15-1.90 (m, 2H); 1.70-1.30 (m, 8H); 0.98 (2d, 6H).

By the general procedures described, or by obvious modifications thereof, the compounds of Tables 1 to 8 can be prepared.

GENERAL STRUCTURE FOR TABLES 1 TO 6 ##STR13##

                  TABLE 1                                                          ______________________________________                                         R.sub.1  R.sub.2        Z.sub.1   R.sub.5                                      ______________________________________                                         CH.sub.3 CH.sub.3       CH.sub.2  H                                            CH.sub.3 CH.sub.3       CH.sub.2  4-F                                          CH.sub.3 CH.sub.3       CH.sub.2  4-Cl                                         CH.sub.3 CH.sub.3       CH.sub.2  4-CH.sub.3                                   CH.sub.3 CH.sub.3       CH.sub.2  6-F                                          CH.sub.3 C.sub.2 H.sub.5                                                                               CH.sub.2  H                                            CH.sub.3 C.sub.2 H.sub.5                                                                               CH.sub.2  4-F                                          CH.sub.3 C.sub.2 H.sub.5                                                                               CH.sub.2  6-F                                          CH.sub.3 i-C.sub.3 H.sub.7                                                                             CH.sub.2  H                                            CH.sub.3 i-C.sub.3 H.sub.7                                                                             CH.sub.2  4-F                                          CH.sub.3 i-C.sub.3 H.sub.7                                                                             CH.sub.2  6-F                                          CH.sub.3 i-C.sub.3 H.sub.7                                                                             CH.sub.2  4-Cl                                         CH.sub.3 i-C.sub.3 H.sub.7                                                                             CH.sub.2  4-CH.sub.3                                   CH.sub.3 i-C.sub.3 H.sub.7                                                                             CH.sub.2  4-OCH.sub.3                                  CH.sub.3 i-C.sub.3 H.sub.7                                                                             CH.sub.2  4-SCH.sub.3                                  CH.sub.3 i-C.sub.3 H.sub.7                                                                             CH.sub. 2 5-CN                                         CH.sub.3 CCl(CH.sub.3).sub.2                                                                           CH.sub.2  H                                            CH.sub.3 CCl(CH.sub.3).sub.2                                                                           CH.sub.2  4-F                                          CH.sub.3 C(CH.sub.3).sub.2 SO.sub.2 CH.sub.3                                                           CH.sub.2  H                                            CH.sub.3 C(CH.sub.3).sub.2 OCH.sub.3                                                                   CH.sub.2  H                                            CH.sub.3 C(CH.sub.3).sub.2 CN                                                                          CH.sub.2  H                                            CH.sub.3 C(CH.sub.3).sub.2 OH                                                                          CH.sub.2  4-Br                                         CH.sub.3 C(CH.sub.3).sub.2 OH                                                                          CH.sub.2  H                                            CH.sub.3 C(CH.sub.3).sub.2 SO.sub.2 Ph                                                                 CH.sub.2  H                                            CH.sub.3 Ph             CH.sub.2  H                                            CH.sub.3 H              CH.sub.2  H                                            CH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3                                                                    CH.sub.2  H                                            CH.sub.3 CH.sub.2 CO.sub.2 H                                                                           CH.sub.2  4-F                                          CH.sub.3 CH.sub.2 Ph    CH.sub.2  H                                            CH.sub.3 CH.sub.2 CHCH.sub.2                                                                           CH.sub.2  H                                            CH.sub.3 CH.sub.2 CHCH.sub.2                                                                           CH.sub.2  4-F                                          CH.sub.3 C(CH.sub.3)CH.sub.2                                                                           CH.sub.2  H                                            CH.sub.3 CH.sub.2 C(CH.sub.3)CH.sub.2                                                                  CH.sub.2  H                                            CH.sub.3 CH.sub.2 CCH   CH.sub.2  H                                            C.sub.2 H.sub.5                                                                         CH.sub.2 C CH  CH.sub.2  H                                            C.sub.2 H.sub.5                                                                         CH.sub.2 CHCH.sub.2                                                                           CH.sub.2  4-F                                          C.sub.2 H.sub.5                                                                         CH.sub.2 CHCH.sub.2                                                                           CH.sub.2  H                                            C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                               CH.sub.2  4-F                                          C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                               CH.sub.2  4-Cl                                         C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                               CH.sub.2  6-F                                          C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                               CH.sub.2  4-CH.sub.3                                   C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                               CH.sub.2  H                                            C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                               O         H                                            C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                               O         4-F                                          C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                               O         4-Cl                                         C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                               O         4-CH.sub.3                                   C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                               O         6-F                                          C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                               O         4,6-di-F                                     C.sub.2 H.sub.5                                                                         CH.sub.2 CHCH.sub.2                                                                           O         H                                            C.sub.2 H.sub.5                                                                         CH.sub.2 CHCH.sub.2                                                                           O         4-F                                          C.sub.2 H.sub.5                                                                         CH.sub.2 CHCH.sub.2                                                                           O         4-Cl                                         C.sub.2 H.sub.5                                                                         CH.sub.2 C(CH.sub.3)CH.sub.2                                                                  O         H                                            C.sub.2 H.sub.5                                                                         CH.sub.2 C(CH.sub.3)CH.sub.2                                                                  O         4-F                                          C.sub.2 H.sub.5                                                                         CH.sub.2 C(CH.sub.3)CH.sub.2                                                                  O         4-CH.sub.3                                   CH.sub.3 CH.sub.2 C(CH.sub.3)CH.sub.2                                                                  O         4-Cl                                         CH.sub.3 CH.sub.2 C(CH.sub.3)CH.sub.2                                                                  O         4-F                                          CH.sub.3 CH.sub.2 C(CH.sub.3)CH.sub.2                                                                  O         H                                            CH.sub.3 i-C.sub.3 H.sub.7                                                                             O         H                                            CH.sub.3 i-C.sub.3 H.sub.7                                                                             O         4,6-di-F                                     CH.sub.3 i-C.sub.3 H.sub.7                                                                             O         4-F                                          CH.sub.3 i-C.sub.3 H.sub.7                                                                             O         4-Cl                                         CH.sub.3 i-C.sub.3 H.sub.7                                                                             O         4-CH.sub.3                                   CH.sub.3 i-C.sub.3 H.sub.7                                                                             S         4-CH.sub.3                                   CH.sub.3 i-C.sub.3 H.sub.7                                                                             S         4-F                                          CH.sub.3 i-C.sub.3 H.sub.7                                                                             S         4-Cl                                         CH.sub.3 i-C.sub.3 H.sub.7                                                                             S         4,6-di-F                                     CH.sub.3 i-C.sub.3 H.sub.7                                                                             S         H                                            C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                               S         H                                            C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                               S         4-CH.sub.3                                   C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                               S         4-F                                          C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                               S         4-Cl                                         C.sub.2 H.sub.5                                                                         CH.sub.2 CHCH.sub.2                                                                           S         H                                            C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                               NCH.sub.3 H                                            CH.sub. 3                                                                               C.sub.2 H.sub.5                                                                               NCH.sub.3 H                                            CH.sub.3 i-C.sub.3 H.sub.7                                                                             NCH.sub.3 H                                            C.sub.2 H.sub.5                                                                         CH.sub.2 CHCH.sub.2                                                                           NCH.sub.3 H                                            ______________________________________                                    

                  TABLE 2                                                          ______________________________________                                          ##STR14##                                                                     R.sub.1     R.sub.2          R.sub.5                                           ______________________________________                                         CH.sub.3    CH.sub.3         H                                                 CH.sub.3    CH.sub.3         4-F                                               CH.sub.3    CH.sub.3         4-Cl                                              CH.sub.3    CH.sub.3         4-CH.sub.3                                        CH.sub.3    CH.sub.3         6-F                                               CH.sub.3    C.sub.2 H.sub.5  H                                                 CH.sub.3    C.sub.2 H.sub.5  4-F                                               CH.sub.3    C.sub.2 H.sub.5  6-F                                               CH.sub.3    i-C.sub.3 H.sub.7                                                                               H                                                 CH.sub.3    i-C.sub.3 H.sub.7                                                                               4-F                                               CH.sub.3    i-C.sub.3 H.sub.7                                                                               6-F                                               CH.sub.3    i-C.sub.3 H.sub.7                                                                               4-Cl                                              CH.sub.3    i-C.sub.3 H.sub.7                                                                               4-CH.sub.3                                        CH.sub.3    i-C.sub.3 H.sub.7                                                                               4-OCH.sub.3                                       CH.sub.3    i-C.sub.3 H.sub.7                                                                               4-SCH.sub.3                                       CH.sub.3    i-C.sub.3 H.sub.7                                                                               5-CN                                              CH.sub.3    CCl(CH.sub.3).sub.2                                                                             H                                                 CH.sub.3    CCl(CH.sub.3).sub.2                                                                             4-F                                               CH.sub.3    C(CH.sub.3).sub.2 SO.sub.2 CH.sub.3                                                             H                                                 CH.sub.3    C(CH.sub.3).sub.2 OCH.sub.3                                                                     H                                                 CH.sub.3    C(CH.sub.3).sub.2 CN                                                                            H                                                 CH.sub.3    C(CH.sub.3).sub.2 OH                                                                            4-Br                                              CH.sub.3    C(CH.sub.3).sub.2 OH                                                                            H                                                 CH.sub.3    C(CH.sub.3).sub.2 SO.sub.2 Ph                                                                   H                                                 CH.sub.3    Ph               H                                                 CH.sub.3    H                H                                                 CH.sub.3    CH.sub.2 CO.sub.2 CH.sub.3                                                                      H                                                 CH.sub.3    CH.sub.2 CO.sub.2 H                                                                             4-F                                               CH.sub.3    CH.sub.2 Ph      H                                                 CH.sub.3    CH.sub.2 CHCH.sub.2                                                                             H                                                 CH.sub.3    CH.sub.2 CHCH.sub.2                                                                             4-F                                               CH.sub.3    C(CH.sub.3)CH.sub.2                                                                             H                                                 CH.sub.3    CH.sub.2 C(CH.sub.3)CH.sub.2                                                                    H                                                 CH.sub.3    CH.sub.2 CCH     H                                                 C.sub.2 H.sub.5                                                                            CH.sub.2 CCH     H                                                 C.sub.2 H.sub.5                                                                            CH.sub.2 CHCH.sub.2                                                                             4-F                                               C.sub.2 H.sub.5                                                                            CH.sub.2 CHCH.sub.2                                                                             H                                                 C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5  4-F                                               C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5  4-Cl                                              C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5  6-F                                               C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5  4-CH.sub.3                                        C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5  H                                                 ______________________________________                                    

                  TABLE 3                                                          ______________________________________                                          ##STR15##                                                                     R.sub.1                                                                              R.sub.2     Z.sub.1  R.sub.5                                             ______________________________________                                         CH.sub.3                                                                             CH.sub.3    O        H                                                   CH.sub.3                                                                             CH.sub.3    O        5-F                                                 CH.sub.3                                                                             CH.sub.3    O        5-CH.sub.3                                          CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                          O        5-CH.sub.3                                          CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                          O        5-Cl                                                CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                          O        5-F                                                 CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                          O        H                                                   CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                          O        5,7-di-F                                            CH.sub.3                                                                             C.sub.2 H.sub.5                                                                            O        H                                                   C.sub.2 H.sub.5                                                                      CH.sub.2 CHCH.sub.2                                                                        O        H                                                   C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                            O        H                                                   C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                            O        5-F                                                 C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                            O        5-Cl                                                C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                            O        5-CH.sub.3                                          C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                            O        5,7-di-F                                            C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                            CH.sub.2 5,7-di-F                                            C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                            CH.sub.2 5-F                                                 C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                            CH.sub.2 5-Cl                                                C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                            CH.sub.2 5-CH.sub.3                                          C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                            CH.sub.2 H                                                   C.sub.2 H.sub.5                                                                      CH.sub.2 CHCH.sub.2                                                                        CH.sub.2 H                                                   C.sub.2 H.sub.5                                                                      CH.sub.2 CHCH.sub.2                                                                        CH.sub.2 5-F                                                 CH.sub.3                                                                             CH.sub.2 CHCH.sub.2                                                                        CH.sub.2 5-F                                                 CH.sub.3                                                                             CH.sub.2 CHCH.sub.2                                                                        CH.sub.2 H                                                   CH.sub.3                                                                             C(CH.sub.3).sub.2 Cl                                                                       CH.sub.2 H                                                   CH.sub.3                                                                             C(CH.sub.3)CH.sub.2                                                                        CH.sub.2 H                                                   CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                          CH.sub.2 5-OCH.sub.3                                         CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                          CH.sub.2 5-CN                                                CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                          CH.sub.2 5-SCH.sub.3                                         CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                          CH.sub.2 H      colorless oil;                                                                 MS (SP/CI) 153                                                                 (9%), 135 (11%),                                                               131 (100%)                                   CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                          CH.sub.2 5-Cl                                                CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                          CH.sub.2 5-CH.sub.3                                          CH.sub. 3                                                                            i-C.sub.3 H.sub.7                                                                          CH.sub.2 5-F                                                 CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                          CH.sub.2 5,7-di-F                                            CH.sub.3                                                                             CH.sub.2 CHCH.sub.2                                                                        CH.sub.2 H                                                   CH.sub.3                                                                             CH.sub.2 CHCH.sub.2                                                                        CH.sub.2 5-F                                                 CH.sub.3                                                                             CH.sub.2 CHCH.sub.2                                                                        CH.sub.2 5-CH.sub.3                                          CH.sub.3                                                                             CH.sub.2 CHCH.sub.2                                                                        CH.sub.2 5-Cl                                                CH.sub.3                                                                             CH.sub.2 CHCH.sub.2                                                                        S        5-Cl                                                CH.sub.3                                                                             CH.sub.2 CHCH.sub.2                                                                        S        5-F                                                 CH.sub.3                                                                             CH.sub.2 CHCH.sub.2                                                                        S        H                                                   C.sub.2 H.sub.5                                                                      CH.sub.2 CHCH.sub.2                                                                        S        H                                                   C.sub.2 H.sub.5                                                                      CH.sub.2 CHCH.sub.2                                                                        S        5-F                                                 C.sub.2 H.sub.5                                                                      CH.sub.2 CHCH.sub.2                                                                        S        5-CH.sub.3                                          C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                            S        5-CH.sub.3                                          C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                            S        5-F                                                 C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                            S        H                                                   C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                            S        5,7-di-F                                            CH.sub.3                                                                             C.sub.2 H.sub.5                                                                            S        H                                                   CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                          S        H                                                   CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                          S        5-F                                                 CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                          S        5-Cl                                                CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                          S        5-CH.sub. 3                                         CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                          S        5,7-di-F                                            CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                          NCH.sub.3                                                                               H                                                   ______________________________________                                    

                  TABLE 4                                                          ______________________________________                                          ##STR16##                                                                     R.sub.1   R.sub.2       Z.sub.1   R.sub.5                                      ______________________________________                                         CH.sub.3  i-C.sub.3 H.sub.7                                                                            S         H                                            CH.sub.3  i-C.sub.3 H.sub.7                                                                            S         5-F                                          CH.sub.3  i-C.sub.3 H.sub.7                                                                            S         5-Cl                                         CH.sub.3  i-C.sub.3 H.sub.7                                                                            S         5-CH.sub.3                                   CH.sub.3  i-C.sub.3 H.sub.7                                                                            S         5,7-di-F                                     CH.sub.3  CH.sub.2 CHCH.sub.2                                                                          S         5,7-di-F                                     CH.sub.3  CH.sub.2 CHCH.sub.2                                                                          S         5-F                                          CH.sub.3  CH.sub.2 CHCH.sub.2                                                                          S         H                                            C.sub.2 H.sub.5                                                                          CH.sub.2 CHCH.sub.2                                                                          S         H                                            C.sub.2 H.sub.5                                                                          CH.sub.2 CHCH.sub.2                                                                          S         5-F                                          C.sub.2 H.sub.5                                                                          CH.sub.2 CHCH.sub.2                                                                          S         5,7-di-F                                     C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                              S         5,7-di-F                                     C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                              S         H                                            C.sub.2 H.sub.5                                                                          C.sub. 2 H.sub.5                                                                             S         5-Cl                                         C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                              S         5-CH.sub.3                                   C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                              S         5-F                                          C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                              O         5-F                                          C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                              O         5-Cl                                         C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                              O         5-CH.sub.3                                   C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                              O         H                                            C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                              O         5,7-di-F                                     C.sub.2 H.sub.5                                                                          CH.sub.2 CHCH.sub.2                                                                          O         H                                            C.sub.2 H.sub.5                                                                          CH.sub.2 CCH  O         H                                            C.sub.2 H.sub.5                                                                          CH.sub.2 CCH  O         5-F                                          CH.sub.3  CH.sub.2 CCH  O         5-F                                          CH.sub.3  CH.sub.2 CCH  O         H                                            CH.sub.3  i-C.sub.3 H.sub.7                                                                            O         H                                            CH.sub.3  i-C.sub.3 H.sub.7                                                                            O         5-Cl                                         CH.sub.3  i-C.sub.3 H.sub.7                                                                            O         5-CH.sub.3                                   CH.sub.3  i-C.sub.3 H.sub.7                                                                            O         5-F                                          CH.sub.3  i-C.sub.3 H.sub.7                                                                            O         5,7-di-F                                     CH.sub.3  i-C.sub.3 H.sub.7                                                                            NC.sub.2 H.sub.5                                                                         H                                            CH.sub.3  i-C.sub.3 H.sub.7                                                                            NH        H                                            CH.sub.3  i-C.sub.3 H.sub.7                                                                            NCH.sub.3 H                                            C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                              NCH.sub.3 H                                            C.sub.2 H.sub.5                                                                          CH.sub.2 CHCH.sub.2                                                                          NCH.sub.3 H                                            ______________________________________                                    

                  TABLE 5                                                          ______________________________________                                          ##STR17##                                                                     R.sub.1                                                                              R.sub.2      Z.sub.1                                                                               g     R.sub.5                                                                               R.sub.6                                 ______________________________________                                         C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                             CH     0     H      H                                       C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                             CH     0     5-F    H                                       C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                             CH     0     5,7-di-F                                                                              H                                       C.sub.2 H.sub.5                                                                      CH.sub.2 CHCH.sub.2                                                                         CH     0     5-CH.sub.3                                                                            H                                       C.sub.2 H.sub.5                                                                      CH.sub.2 CHCH.sub.2                                                                         CH     0     5-F    H                                       C.sub.2 H.sub.5                                                                      CH.sub.2 CHCH.sub.2                                                                         CH     0     H      H                                       CH.sub.3                                                                             CH.sub.2 CHCH.sub.2                                                                         CH     0     H      H                                       CH.sub.3                                                                             CH.sub.2 CHCH.sub.2                                                                         CH     0     5-F    H                                       CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                           CH     0     5-F    H                                       CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                           CH     0     5,7-di-F                                                                              H                                       CH.sub.3                                                                             i-C.sub.3 H.sub. 7                                                                          CH     0     H      H                                       CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                           CH     1     H      H                                       CH.sub.3                                                                             CH.sub.2 CHCH.sub.2                                                                         CH     1     H      H                                       C.sub.2 H.sub.5                                                                      CH.sub.2 CHCH.sub.2                                                                         CH     1     H      H                                       C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                             CH     1     H      H                                       C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                             N      1     H      H                                       C.sub.2 H.sub.2                                                                      CH.sub.2 CHCH.sub.2                                                                         N      1     H      H                                       CH.sub.3                                                                             CH.sub.2 CHCH.sub.2                                                                         N      1     H      H                                       CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                           N      1     H      H                                       CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                           N      1     H      OCH.sub.3                               ______________________________________                                    

                  TABLE 6                                                          ______________________________________                                          ##STR18##                                                                     R.sub.1      R.sub.2         R.sub.6                                           ______________________________________                                         C.sub.2 H.sub.5                                                                             C.sub.2 H.sub.5 H                                                 C.sub.2 H.sub.5                                                                             C.sub.2 H.sub.5 OCH.sub.3                                         C.sub.2 H.sub.5                                                                             CH.sub.2 CHCH.sub.2                                                                            OCH.sub.3                                         C.sub.2 H.sub.5                                                                             CH.sub.2 CHCH.sub.2                                                                            H                                                 CH.sub.3     CH.sub.2 CHCH.sub.2                                                                            H                                                 CH.sub.3     CH.sub.2 CHCH.sub.2                                                                            OCH.sub.3                                         CH.sub.3     i-C.sub.3 H.sub.7                                                                              OCH.sub.3                                         CH.sub.3     i-C.sub.3 H.sub.7                                                                              H                                                 ______________________________________                                    

                  TABLE 7                                                          ______________________________________                                          ##STR19##                                                                     R.sub.1                                                                             R.sub.2     X        Y       ZZ.sup.1                                     ______________________________________                                         CH.sub.3                                                                            H           CH.sub.2 C(CH.sub.3).sub.2                                                                      CH.sub.2 CH.sub.2 CH.sub.2                   CH.sub.3                                                                            H           CH.sub.2 C(C.sub.2 H.sub.5).sub.2                                                               CH.sub.2 CH.sub.2 CH.sub.2                   CH.sub.3                                                                            H           CH.sub.2                                                                                 ##STR20##                                                                             CH.sub.2 CH.sub.2 CH.sub.2                   CH.sub.3                                                                            H           CH.sub.2                                                                                 ##STR21##                                                                             CH.sub.2 CH.sub.2 CH.sub.2                   C.sub.2 H.sub.5                                                                     H           CH.sub.2 C(C.sub.2 H.sub.5).sub.2                                                               CH.sub.2 CH.sub.2 CH.sub.2                   CH.sub.3                                                                            H           CH.sub.2 C(CH.sub.3).sub.2                                                                      CH.sub.2 CH.sub.2                            CH.sub.3                                                                            H           CH.sub.2 C(C.sub.2 H.sub.5 ).sub.2                                                              CH.sub.2 CH.sub.2                            CH.sub.3                                                                            H           --       C(CH.sub.3).sub.2                                                                      CH.sub.2 CH.sub.2 CH.sub.2                   CH.sub.3                                                                            CH.sub.3    CH.sub.2 --      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2          CH.sub.3                                                                            H           CH.sub.2 CH.sub.2                                                                       C(CH.sub.3).sub.2                                                                      CH.sub.2 CH.sub.2                            CH.sub.3                                                                            H           CH.sub.2 CH.sub.2                                                                       C(C.sub.2 H.sub.5).sub.2                                                               CH.sub.2 CH.sub.2                            CH.sub.3                                                                            H           CH.sub.2 CH.sub.2                                                                       C(CH.sub.3).sub.2                                                                      CH.sub.2 CH.sub.2                            C.sub.2 H.sub.5                                                                     H           CH.sub.2 CH.sub.2                                                                       C(CH.sub.3).sub.2                                                                      CH.sub.2 CH.sub.2                            C.sub.2 H.sub.5                                                                     H           CH.sub.2 CH.sub.2                                                                       C(C.sub.2 H.sub.5).sub.2                                                               CH.sub.2 CH.sub.2                            CH.sub.3                                                                            H           CH.sub.2 CH.sub.2                                                                       C(C.sub.2 H.sub.5).sub.2                                                               CH.sub.2 CH.sub.2                            CH.sub.3                                                                            H           CH.sub.2 CH.sub.2                                                                        ##STR22##                                                                             CH.sub.2 CH.sub.2                            CH.sub.3                                                                            H           CH.sub.2 CH.sub.2                                                                        ##STR23##                                                                             CH.sub.2 CH.sub.2                            C.sub.2 H.sub.5                                                                     H           CH.sub.2 CH.sub.2                                                                        ##STR24##                                                                             CH.sub.2 CH.sub.2                            C.sub.2 H.sub.5                                                                     H           CH.sub.2 CH.sub.2                                                                        ##STR25##                                                                             CH.sub.2 CH.sub.2                            CH.sub.3                                                                            CH.sub.3    CH.sub.2 CH.sub.2                                                                       --      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2          C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                            CH.sub.2 CH.sub.2                                                                       --      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2          C.sub.2 H.sub.5                                                                     CH.sub.2 CHCH.sub.2                                                                        CH.sub.2 CH.sub.2                                                                       --      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2          CH.sub.3                                                                            CH(CH.sub.3).sub.2                                                                         CH.sub.2 CH.sub.2                                                                       --      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2          CH.sub.3                                                                            H           CH.sub.2 C(CH.sub.3).sub.2                                                                      CH.sub.2 CH.sub.2 O                          CH.sub.3                                                                            H           CH.sub.2 C(C.sub.2 H.sub.5).sub.2                                                               CH.sub.2 CH.sub.2 O                          CH.sub.3                                                                            H           CH.sub.2                                                                                 ##STR26##                                                                             CH.sub.2 CH.sub.2 O                          C.sub.2 H.sub.5                                                                     H           CH.sub.2                                                                                 ##STR27##                                                                             CH.sub.2 CH.sub.2 O                          C.sub.2 H.sub.5                                                                     H           CH.sub.2 C(C.sub.2 H.sub.5).sub.2                                                               CH.sub.2 CH.sub.2 O                          CH.sub.3                                                                            H           CH.sub.2 C(CH.sub.3).sub.2                                                                      CH.sub.2 O                                   CH.sub.3                                                                            H           CH.sub.2 C(C.sub.2 H.sub.5).sub.2                                                               CH.sub.2 O                                   CH.sub.3                                                                            H           --       C(CH.sub.3).sub.2                                                                      CH.sub.2 CH.sub.2 O                          CH.sub.3                                                                            H           CH.sub.2 CH.sub.2                                                                       --      CH.sub.2 CH.sub.2 CH.sub.2 O                 CH.sub.3                                                                            H           CH.sub.2 CH.sub.2                                                                       C(CH.sub.3).sub.2                                                                      CH.sub.2 O                                   CH.sub.3                                                                            H           CH.sub.2 CH.sub.2                                                                       C(C.sub.2 H.sub.5).sub.2                                                               CH.sub.2 O                                   CH.sub.3                                                                            H           CH.sub.2 CH.sub.2                                                                       C(CH.sub.3).sub.2                                                                      CH.sub.2 O                                   C.sub.2 H.sub.5                                                                     H           CH.sub.2 CH.sub.2                                                                       C(CH.sub.3).sub.2                                                                      CH.sub.2 O                                   C.sub.2 H.sub.5                                                                     H           CH.sub.2 CH.sub.2                                                                       C(CH.sub.3).sub.2                                                                      CH.sub.2 O                                   C.sub.2 H.sub.5                                                                     H           CH.sub.2 CH.sub.2                                                                       C(C.sub.2 H.sub.5).sub.2                                                               CH.sub.2 O                                   CH.sub.3                                                                            H           CH.sub.2 CH.sub.2                                                                       C(C.sub.2 H.sub.5).sub.2                                                               CH.sub.2 O                                   CH.sub.3                                                                            H           CH.sub.2 CH.sub.2                                                                        ##STR28##                                                                             CH.sub.2 O                                   CH.sub.3                                                                            H           CH.sub.2 CH.sub.2                                                                        ##STR29##                                                                             CH.sub.2 O                                   C.sub.2 H.sub.5                                                                     H           CH.sub.2 CH.sub.2                                                                        ##STR30##                                                                             CH.sub.2 O                                   C.sub.2 H.sub.5                                                                     H           CH.sub.2 CH.sub.2                                                                        ##STR31##                                                                             CH.sub.2 O                                   CH.sub.3                                                                            CH.sub.3    CH.sub.2 CH.sub.2                                                                       --      CH.sub.2 CH.sub.2 CH.sub.2 O                 C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                            CH.sub.2 CH.sub.2                                                                       --      CH.sub.2 CH.sub.2 CH.sub.2 O                 C.sub.2 H.sub.5                                                                     CH.sub.2 CHCH.sub.2                                                                        CH.sub.2 CH.sub.2                                                                       --      CH.sub.2 CH.sub.2 CH.sub.2 O                 ______________________________________                                    

                  TABLE 8                                                          ______________________________________                                          ##STR32##                                                                     R.sub.1                                                                              R.sub.2     X        Y        Z                                          ______________________________________                                         CH.sub.3                                                                             H           CH.sub.2 C(CH.sub.3).sub.2                                                                       CH.sub.2 CH.sub.2                          CH.sub.3                                                                             H           CH.sub.2 C(C.sub.2 H.sub.5).sub.2                                                                CH.sub.2 CH.sub.2                          CH.sub.3                                                                             H           CH.sub.2                                                                                 ##STR33##                                                                              CH.sub.2 CH.sub.2                          CH.sub.3                                                                             H           CH.sub.2                                                                                 ##STR34##                                                                              CH.sub.2 CH.sub.2                          C.sub.2 H.sub.5                                                                      H           CH.sub.2 C(C.sub.2 H.sub.5).sub.2                                                                CH.sub.2 CH.sub.2                          CH.sub.3                                                                             H           CH.sub.2 C(CH.sub.3).sub.2                                                                       CH.sub.2                                   CH.sub.3                                                                             H           CH.sub.2 C(C.sub.2 H.sub.5).sub.2                                                                CH.sub.2                                   CH.sub.3                                                                             H           --       C(CH.sub.3).sub.2                                                                       CH.sub.2 CH.sub.2                          CH.sub.3                                                                             CH.sub.3    CH.sub.2 --       CH.sub.2 CH.sub.2 CH.sub.2                 CH.sub. 3                                                                            H           CH.sub.2 CH.sub.2                                                                       C(CH.sub.3).sub.2                                                                       CH.sub.2                                   CH.sub.3                                                                             H           CH.sub.2 CH.sub.2                                                                       C(C.sub.2 H.sub.5).sub.2                                                                CH.sub.2                                   CH.sub.3                                                                             H           CH.sub.2 CH.sub.2                                                                       C(CH.sub.3).sub.2                                                                       CH.sub.2                                   C.sub.2 H.sub.5                                                                      H           CH.sub.2 CH.sub.2                                                                       C(CH.sub.3).sub.2                                                                       CH.sub.2                                   C.sub.2 H.sub.5                                                                      H           CH.sub.2 CH.sub.2                                                                       C(CH.sub.2 CH.sub.3)                                                                    CH.sub.2                                   CH.sub.3                                                                             H           CH.sub.2 CH.sub.2                                                                       C(C.sub.2 H.sub.5).sub.2                                                                CH.sub.2                                   CH.sub.3                                                                             H           CH.sub.2 CH.sub.2                                                                        ##STR35##                                                                              CH.sub.2                                   CH.sub.3                                                                             H           CH.sub.2 CH.sub.2                                                                        ##STR36##                                                                              CH.sub.2                                   C.sub.2 H.sub.5                                                                      H           CH.sub.2 CH.sub.2                                                                        ##STR37##                                                                              CH.sub.2                                   C.sub.2 H.sub.5                                                                      H           CH.sub.2 CH.sub.2                                                                        ##STR38##                                                                              CH.sub.2                                   CH.sub.3                                                                             CH.sub.3    CH.sub.2 CH.sub.2                                                                       --       CH.sub.2 CH.sub.2 CH.sub.2                 C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                            CH.sub.2 CH.sub.2                                                                       --       CH.sub.2 CH.sub.2 CH.sub.2                 C.sub.2 H.sub.5                                                                      CH.sub. 2 CHCH.sub.2                                                                       CH.sub.2 CH.sub.2                                                                       --       CH.sub.2 CH.sub.2 CH.sub.2                 ______________________________________                                    

                                      TABLE 9                                      __________________________________________________________________________      ##STR39##                                                                     R.sub.1                                                                            R.sub.2  X     Y      Z       Z.sup.1                                      __________________________________________________________________________     CH.sub.3                                                                           H        CH.sub.2                                                                             C(CH.sub.3).sub.2                                                                     CH.sub.2 CH.sub.2                                                                      CH.sub.2 CH.sub.2                            CH.sub.3                                                                           H        CH.sub.2                                                                             C(C.sub.2 H.sub.5).sub.2                                                              CH.sub.2 CH.sub.2                                                                      CH.sub.2 CH.sub.2                            CH.sub.3                                                                           H        CH.sub.2                                                                              ##STR40##                                                                            CH.sub.2 CH.sub.2                                                                      CH.sub.2 CH.sub.2                            CH.sub.3                                                                           H        CH.sub.2                                                                              ##STR41##                                                                            CH.sub.2 CH.sub.2                                                                      CH.sub.2 CH.sub.2                            C.sub.2 H.sub.5                                                                    H        CH.sub.2                                                                             C(C.sub.2 H.sub.5).sub.2                                                              CH.sub.2 CH.sub.2                                                                      CH.sub.2 CH.sub.2                            CH.sub.3                                                                           H        CH.sub.2                                                                             C(CH.sub.3).sub.2                                                                     CH.sub. 2                                                                              CH.sub.2 CH.sub.2                            CH.sub.3                                                                           H        CH.sub.2                                                                             C(C.sub.2 H.sub.5).sub.2                                                              CH.sub.2                                                                               CH.sub.2 CH.sub.2                            CH.sub.3                                                                           H        --    C(CH.sub.3).sub.2                                                                     CH.sub.2 CH.sub.2                                                                      CH.sub.2 CH.sub.2                            CH.sub.3                                                                           CH.sub.3 CH.sub.2                                                                             --     CH.sub.2 CH.sub.2 CH.sub.2                                                             CH.sub.2 CH.sub.2                            CH.sub.3                                                                           H        CH.sub.2 CH.sub.2                                                                    C(CH.sub.3).sub.2                                                                     CH.sub.2                                                                               CH.sub.2 CH.sub.2                            CH.sub.3                                                                           H        CH.sub.2 CH.sub.2                                                                    C(C.sub.2 H.sub.5).sub.2                                                              CH.sub.2                                                                               CH.sub.2 CH.sub.2                            CH.sub.3                                                                           H        CH.sub.2 CH.sub.2                                                                    C(CH.sub.3).sub.2                                                                     CH.sub.2                                                                               CH.sub.2 CH.sub.2                            C.sub.2 H.sub.5                                                                    H        CH.sub.2 CH.sub.2                                                                    C(CH.sub.3).sub.2                                                                     CH.sub.2                                                                               CH.sub.2 CH.sub.2                            C.sub.2 H.sub.5                                                                    H        CH.sub.2 CH.sub.2                                                                    C(C.sub.2 H.sub.5).sub.2                                                              CH.sub.2                                                                               CH.sub.2 CH.sub.2                            CH.sub.3                                                                           H        CH.sub.2 CH.sub.2                                                                    C(C.sub.2 H.sub.5).sub.2                                                              CH.sub.2                                                                               CH.sub.2 CH.sub.2                            CH.sub.3                                                                           H        CH.sub.2 CH.sub.2                                                                     ##STR42##                                                                            CH.sub.2                                                                               CH.sub.2 CH.sub.2                            CH.sub.3                                                                           H        CH.sub.2 CH.sub.2                                                                     ##STR43##                                                                            CH.sub.2                                                                               CH.sub.2 CH.sub.2                            C.sub.2 H.sub.5                                                                    H        CH.sub.2 CH.sub.2                                                                     ##STR44##                                                                            CH.sub.2                                                                               CH.sub.2 CH.sub.2                            C.sub.2 H.sub.5                                                                    H        CH.sub.2 CH.sub.2                                                                     ##STR45##                                                                            CH.sub.2                                                                               CH.sub.2 CH.sub.2                            CH.sub.3                                                                           CH.sub.3 CH.sub.2 CH.sub.2                                                                    --     CH.sub.2 CH.sub.2 CH.sub.2                                                             CH.sub.2 CH.sub.2                            C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                         CH.sub.2 CH.sub.2                                                                    --     CH.sub.2 CH.sub.2 CH.sub.2                                                             CH.sub.2 CH.sub.2                            C.sub.2 H.sub.5                                                                    CH.sub.2 CHCH.sub.2                                                                     CH.sub.2 CH.sub.2                                                                    --     CH.sub.2 CH.sub.2 CH.sub.2                                                             CH.sub.2 CH.sub.2                            CH.sub.3                                                                           H        CH.sub.2                                                                              ##STR46##                                                                            CH.sub.2 CH.sub.2                                                                      CH.sub.2 O                                   C.sub.2 H.sub.5                                                                    H        CH.sub.2                                                                              ##STR47##                                                                            CH.sub.2 CH.sub.2                                                                      CH.sub.2 O                                   C.sub.2 H.sub.5                                                                    H        CH.sub.2                                                                             C(C.sub.2 H.sub.5).sub.2                                                              CH.sub.2 CH.sub.2                                                                      CH.sub.2 O                                   CH.sub.3                                                                           H        CH.sub.2                                                                             C(CH.sub.3).sub.2                                                                     CH.sub. 2                                                                              CH.sub.2 O                                   CH.sub.3                                                                           H        CH.sub.2                                                                             C(C.sub.2 H.sub.5).sub.2                                                              CH.sub.2                                                                               CH.sub.2 O                                   CH.sub.3                                                                           H        --    C(CH.sub.3).sub.2                                                                     CH.sub.2 CH.sub.2                                                                      CH.sub.2 O                                   CH.sub.3                                                                           H        CH.sub.2 CH.sub.2                                                                    --     CH.sub.2 CH.sub.2 CH.sub.2                                                             CH.sub.2 O                                   CH.sub.3                                                                           H        CH.sub.2 CH.sub.2                                                                    C(CH.sub.3).sub.2                                                                     CH.sub.2                                                                               CH.sub.2 O                                   CH.sub.3                                                                           H        CH.sub.2 CH.sub.2                                                                    C(C.sub.2 H.sub.5).sub.2                                                              CH.sub.2                                                                               CH.sub.2 O                                   CH.sub.3                                                                           H        CH.sub.2 CH.sub.2                                                                    C(CH.sub.3).sub.2                                                                     CH.sub.2                                                                               CH.sub.2 O                                   C.sub.2 H.sub.5                                                                    H        CH.sub.2 CH.sub.2                                                                    C(CH.sub.3).sub.2                                                                     CH.sub.2                                                                               CH.sub.2 O                                   C.sub.2 H.sub.5                                                                    H        CH.sub.2 CH.sub.2                                                                    C(CH.sub.3).sub.2                                                                     CH.sub.2                                                                               CH.sub.2 O                                   C.sub.2 H.sub.5                                                                    H        CH.sub.2 CH.sub.2                                                                    C(C.sub.2 H.sub.5).sub.2                                                              CH.sub.2                                                                               CH.sub.2 O                                   CH.sub.3                                                                           H        CH.sub.2 CH.sub.2                                                                    C(C.sub.2 H.sub.5).sub.2                                                              CH.sub.2                                                                               CH.sub.2 O                                   CH.sub.3                                                                           H        CH.sub.2 CH.sub.2                                                                     ##STR48##                                                                            CH.sub.2                                                                               CH.sub.2 O                                   CH.sub. 3                                                                          H        CH.sub.2 CH.sub.2                                                                     ##STR49##                                                                            CH.sub.2                                                                               CH.sub.2 O                                   C.sub.2 H.sub.5                                                                    H        CH.sub.2 CH.sub.2                                                                     ##STR50##                                                                            CH.sub.2                                                                               CH.sub.2 O                                   C.sub.2 H.sub.5                                                                    H        CH.sub.2 CH.sub.2                                                                     ##STR51##                                                                            CH.sub.2                                                                               CH.sub.2 O                                   CH.sub.3                                                                           CH.sub.3 CH.sub.2 CH.sub.2                                                                    --     CH.sub.2 CH.sub.2 CH.sub.2                                                             CH.sub.2 O                                   C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                         CH.sub.2 CH.sub.2                                                                    --     CH.sub.2 CH.sub.2 CH.sub.2                                                             CH.sub.2 O                                   C.sub.2 H.sub.5                                                                    CH.sub.2 CHCH.sub.2                                                                     CH.sub.2 CH.sub.2                                                                    --     CH.sub.2 CH.sub.2 CH.sub.2                                                             CH.sub.2 O                                   __________________________________________________________________________

FORMULATIONS

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:

                  TABLE 9                                                          ______________________________________                                                     Active  Weight Percent*                                                        Ingredient                                                                             Diluent(s)                                                                               Surfactant(s)                                    ______________________________________                                         Wettable Powders                                                                             5-60      39-94     1-10                                         Emulsifiable  3-80      20-95     0-20                                         Concentrates                                                                   Dusts         1-25      70-99     0-5                                          Granules and Pellets                                                                         0.1-50      50-99.9 0-15                                         ______________________________________                                          *Active ingredient plus at least one of a Surfactant or a Diluent equals       100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J., but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, Jun. 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.

EXAMPLE A Wettable Powder

    ______________________________________                                         7-oxabicyclo((2.2.1))heptane' 2-(2,3-dihydro-                                                              60%                                                1H-inden-1-yloxy)-1-methyl-4-(1-methylethyl)                                   sodium alkylnaphthalenesulfonate                                                                            2%                                                sodium ligninsulfonate       2%                                                synthetic amorphous silica  36%                                                ______________________________________                                    

The active ingredient is first sprayed onto the amorphous silica, then the ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.

EXAMPLE B Wettable Powder

    ______________________________________                                         7-oxabicyclo((2.2.1))heptane' 2-(2,3-dihydro-                                                              50%                                                1H-inden-1-yloxy)-1-methyl-4-(1-methylethyl)                                   sodium alkylnaphthalenesulfonate                                                                            2%                                                low viscosity methyl cellulose                                                                              2%                                                diatomaceous earth          46%                                                ______________________________________                                    

The active ingredient is first sprayed onto the diatomaceous earth then the ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.

EXAMPLE C Granule

    ______________________________________                                         Wettable Powder of Example 4                                                                              5%                                                  attapulgite granules      95%                                                  (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                              ______________________________________                                    

A slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.

EXAMPLE D Emulsifiable Concentrate

    ______________________________________                                         7-oxabicyclo((2.2.1))heptane' 2-(2,3-dihydro-                                                              40%                                                1H-inden-1-yloxy)-1-methyl-4-(1-methylethyl)                                   Atlox 3403F                  3%                                                Atlox 3404F                  3%                                                xylene                      54%                                                ______________________________________                                    

The active ingredient and Atlox emulsifiers are dissolved in the solvent, filtered and packaged. Atlox 3403F and 3404F are blends of anionic and ionic emulsifiers from ICI Americas, Inc.

EXAMPLE E Low Strength Granule

    ______________________________________                                         7-oxabicyclo((2.2.1))heptane' 2-(2,3-dihydro-                                                               5%                                                1H-inden-1-yloxy)-1-methyl-4-(1-methylethyl)                                   atapulgite granules         95%                                                (U.S.S. 20-40 mesh)                                                            ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.

EXAMPLE F Granule

    ______________________________________                                         7-oxabicyclo((2.2.1))heptane' 2-(2,3-dihydro-                                                              50%                                                1H-inden-1-yloxy)-1-methyl-4-(1-methylethyl)                                   wetting agent                1%                                                crude ligninsulfonate salt (containing                                                                     10%                                                5-20% of the natural sugars)                                                   attapulgite clay            39%                                                ______________________________________                                    

The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.

EXAMPLE G Concentrated Emulsion

    ______________________________________                                         7-oxabicyclo((2.2.1))heptane' 2-(2,3-dihydro-                                                              25%                                                1H-inden-1-yloxy)-1-methyl-4-(1-methylethyl)                                   xylene                      25%                                                Atlox 3404F                  5%                                                G1284                        5%                                                ethylene glycol              8%                                                water                       32%                                                ______________________________________                                    

The active ingredient, solvent and emulsifiers are blended together. This solution is added to a mixture of the ethylene glycol and water with stirring.

EXAMPLE H Solution

    ______________________________________                                         7-oxabicyclo((2.2.1))heptane' 2-(2,3-dihydro-                                                               5%                                                1H-inden-1-yloxy)-1-methyl-4-(1-methylethyl)                                   water                       95%                                                ______________________________________                                    

The compound is added directly to the water with stirring to produce the solution, which may then be packaged for use.

EXAMPLE I Dust

    ______________________________________                                         7-oxabicyclo((2.2.1))heptane' 2-(2,3-dihydro-                                                              10%                                                1H-inden-1-yloxy)-1-methyl-4-(1-methylethyl)                                   attapulgite                 10%                                                Pyrophyllite                80%                                                ______________________________________                                    

The active ingredient is sprayed onto the attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous.

UTILITY

Test results indicate that compounds of this invention are highly active preemergent and/or postemergent herbicides or plant growth regulants. These compounds are useful for postemergence grass control in agronomic crops and are particularly useful for preemergence broad-spectrum grass and selected small-seeded broadleaf weed control in agronomic crops. Agronomic crops such as barley (Hordeum vulgare), corn (Zea mays), cotton (Gossypium hirsutum), rape (Brassica napus), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), and wheat (Triticum aestivum) show little or no injury when treated with application rates necessary for weed control for many of the compounds in this invention. Many of the compounds of this invention are also particularly suitable for barnyardgrass (Echinochloa crus-galli) control in transplanted rice. Troublesome weed species that are suppressed or controlled are grass weeds such as barnyardgrass (Echinochloa crus-galli), blackgrass (Alopecurus myosuroides), cheatgrass (Bromus secalinus), crabgrass (Digitaria spp.), downy brome (Bromus tectorum), foxtail (Setaria spp.), johnsongrass (Sorghum halepense), and wild oat (Avena fatua); broadleaf weeds such as lambsquarters (Chenopodium album) and velvetleaf (Abutilon theophrasti); and sedge (Cyperus spp.).

Test results also indicate that compounds of this invention have utility for broad-spectrum pre-and/or postemergence weed control in other areas where control of vegetation is desired, such as around storage tanks, parking lots, drive-in theaters, billboards, highways, and railroad structures and in fallow areas of crop production such as in wheat, barley, and in plantation crops such as palm, pineapple, plantin, banana, citrus, rubber, sugarcane, etc.

Rates of application for compounds of this invention are determined by a number of factors. These factors include: formulation selected, method of application, amount of vegetation present, growing conditions, etc. In general terms, the subject compounds should be applied at rates from 0.01 to 20 kg/ha with a preferred rate range of from 0.05 to 1 kg/ha. One skilled in the art can easily determine rates needed for the desired level of weed control.

Compounds of this invention may be used alone or in combination with other commercial herbicides, insecticides, or fungicides. The following list exemplifies some of the herbicides suitable for use in mixtures. A combination of a compound from this invention with one or more of the following herbicides may be particularly useful for weed control.

    ______________________________________                                         Common Name                                                                               Chemical Name                                                       ______________________________________                                         acetochlor 2-chloro-B-(ethoxymethyl)-N-(2-ethyl-                                          6-methylphenyl)acetamide                                            acifluorfen                                                                               5-[2-chloro-4-(trifluoromethyl)phenoxy]-                                       2-nitrobenzoic acid                                                 acrolein   2-propenal                                                          alachlor   2-chloro-2,6-diethylphenyl-N-(methoxy                                          methyl)acetanilide                                                  ametryn    N-ethyl-N'-1(1-methylethyl)-6-(methyl-                                         thio)-1,3,5-triazine-2,4-diamine                                    amitrole   1H-1,2,4-triazol-3-amine                                            AMS        ammonium sulfamate                                                  asulam     methyl [(4-aminophenyl)sulfonyl]carbamate                           atrazine   6-chloro-N-ethyl-N'-(1methylethyl)-1,3,5-                                      triazine-2,4-diamine                                                barban     4-chloro-2-butynyl 3-chlorophenylcarbamate                          benefin    N-butyl-N-ethyl-2,6-dinitro-4-(tri-                                            fluoromethyl)benzenamine                                            bensulfuron                                                                               2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)-                               methyl     amino]carbonyl]amino]sulfonyl]methyl]-                                         benzoic acid, methyl ester                                          bensulide  O,O-bis(1-methylethyl)S-[2-[(phenylsulfonyl)-                                  amino]ethyl]phosphorodithioate                                      bentazon   3-(1-methylethyl)-(1H)-2,23-benzothiadiazinO                                   4(3H)-one 2,2-dioxide                                               benzofluor N-[4-(ethylthio)-2-(trifluoromethyl)phenyl]-                                   methanesulfonamide                                                  benzoylprop                                                                               N-benzoyl-N-(3,4-dichlorophenyl)-DL-                                           alaine                                                              bifenox    methyl 5-(2,4-dichlorophenoxy)-2-                                              nitrobenzoate                                                       bromacil   5-bromo-6-methyl-3-(1-methylpropyl)-2,4-                                       (1H,3H)pyrimidinedione                                              bromoxynil 3,5-dibromo-4-hydroxybenzonitrile                                   butachlor  N-(butoxymethyl)-2-chloro-N-(2,6-diethyl-                                      phenyl)acetamide                                                    buthidazole                                                                               3-[5-(1,1-dimethylethyl)-1,3,4-thiadia-                                        zol-2-yl]-4-hydroxy-1-methyl-2-imida-                                          zolidinone                                                          butralin   4-(1,1-dimethylethyl)-N-(1-methyl-                                             propyl)-2,6-dinitrobenzenamine                                      butylate   S-ethyl-bis(2-methylpropyl)carbamothioate                           cacodylic  dimethyl arsinic acid                                               acid                                                                           CDAA       2-chloro-N,N-di-2-propenylacetamide                                 CDEC       2-chloroallyl diethyldithiocarbamate                                chloramben 3-amino-2,5-dichlorobenzoic acid                                    chlorbromuron                                                                             3-(4-bromo-3-chlorophenyl)-1-methoxy-1-                                        methylurea                                                          chlorimuron                                                                               2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)-                           ethyl      amino]carbonyl]amino]sulfonyl]benzoic-                                         acid, ethyl ester                                                   chloroxuron                                                                               N'-[4-(4-chlorophenoxy)phenyl]-N,N-                                            dimethylurea                                                        chlorpropham                                                                              1-methylethyl 3-chlorophenylcarbamate                               chlorsulfuron                                                                             2-chloro-N-[(4-methoxy-6-methyl-1,3,5-                                         triazin-2-yl)amino]carbonyl]benzene-                                           sulfonamide                                                         chlortoluron                                                                              N'-(3-chloro-4-methylphenyl-N,N-                                               dimethylurea                                                        cinmethylin                                                                               exo-1-methyl-4-(1-methylethyl)-2-                                              [(2-methylphenyl)methoxy]-7-                                                   oxabicyclo[2.2.1]heptane                                            clethodim  (E,E)-(%)-2-[[(3-chloro-2-prophenyl)oxy]-                                      imino]propyl]-5-[2-(ethylthio)-propyl]-                                        3-hydroxy-2-cyclohexan-1-one                                        clomazone  2-[(2-chlorophenyl(methyl]-4,4-dimethyl-                                       3-isoxazolidinone                                                   cloproxydim                                                                               (E,E)-2-[1-[[(3-chloro-2-propenyl)oxy)                                         imino[butyl]-5-[2-(ethylthio)propyl]-                                          3-hydroxy-2-cyclohexen-1-one                                        clopyralid 3,6-dichloro-2-pyridinecarboxylic acid                              CMA        calcium salt of MAA                                                 cyanazine  2-[[4-chloro-6-(ethylamino)-1,3,5-                                             triazin-2-yl]amino]-2-methyl-                                                  propanenitrile                                                      cycloate   S-ethyl cyclohexylethylcarbamothioate                               cycluron   3-cyclooctyl-1,1-dimethylurea                                       cyperquat  1-methyl-4-phenylpyridinium                                         cyprazine  2-chloro-4-(cyclopropylamino)-6-(iso-                               cypromid   3',4'-dichlorocyclopropanecarboxanilide                             dalapon    2,2-dichloropropionic acid                                          dalapon    2,2-dichloropropanoic acid                                          dazomet    tetrahydro-3,5-dimethyl-2H-1,3,5-thia-                                         diazine-2-thione                                                    DCPA       dimethyl 2,3,5,6-tetrachloro-1,4-                                              benzenedicarboxylate                                                desmediphan                                                                               ethyldesmetryn[3-[[(phenylamino)-                                              carbonyl]oxy]phenyl]carbamate                                       desmetryn  2-(isopropylamino)-4-(methylamino)-6-                               diallate   S-(2,3-dichloro-2-propenyl) bis(1-methyl-                                      ethyl)carbamothioate                                                dicamba    3,6-dichloro-2-methoxybenzoic acid                                  dichlobenil                                                                               2,6-dichlorobenzonitrile                                            dichlorprop                                                                               (%)-2-(2,4-dichlorophenoxy)propanoic acid                           diclofop   (%)-2-[4-(2,4-dichlorophenoxy)phenoxy]  -                                      propanoic acid                                                      diethatyl  N-(chloroacetyl)-N-(2,6-diethylphenyl)-                                        glycine                                                             difenzoquat                                                                               1,2-dimethyl-3,5-diphenyl-1H-pyrazolium                             dinitramine                                                                               N.sup.3,N.sup.3 -diethyl-2,4-dinitro-6-(tri-                                   fluoromethyl)-1,3-benzenediamine                                    dinoseb    2-(1-methylpropyl)-4,6-dinitrophenol                                diphenamide                                                                               N,N-dimethyl-a-phenylbenzeneacetamide                               dipropetryn                                                                               6-(ethylthio)-N,N'-bis (1-methylethyl)-                                        1,3,5-triazine-2,4-diamine                                          diquat     6,7-dihydrodipyrido[1,2-a:2',1'-c]-                                            pyrazinediium ion                                                   diuron     N'-(3,4-dichlorophenyl)-N,N-dimethylurea                            DNOC       2-methyl-4,6-dinitrophenol                                          DPX-M6316  3-DSMA[[[[(4-methoxy-6-methyl-1,3,5-                                           triazin-2-yl)amino]carbonyl]amino]-                                            sulfonyl]-2-thiophenecarboxylic acid,                                          methyl ester                                                        DPX-V9360  2-[[[[(4,6-dimethoxypyrimidin-2-yl)-                                           amino]carbonyl]amino]sulfonyl]-                                                3-pyridinecarboxylic acid,                                                     N,N-dimethylamide                                                   DSMA       disodium salt of MAA                                                endothall  7-oxabicyclo[2.2.1]heptane-2,3-dicarbox-                                       ylic acid                                                           EPTC       S-ethyl diproprylcarbamothioate                                     ethafluralin                                                                              N-ethyl-N-(2-methyl-2-propenyl)-2,6-                                           dinitro-4-(trifluoromethyl)benzen-                                             amine                                                               ethofumesate                                                                              (±)-2-ethoxy-2,3-dihydro-3,3-dimethyl-                                      5-benzofuranyl methanesulfonate                                     Express*   2[[[[N-(4-methoxy-6-methyl-                                                    1,3,5-triazine-2-yl)-N-methylamino]-                                           carbonyl]amino]sulfonyl]benzoic acid,                                          methyl ester                                                        fenac      2,3,6-trichlorophenylacetic acid                                    fenoxaprop (%)-2-[4-[6-chloro-2-benzoxazolyl-                                  ethyl      oxy]phenoxy]propanoic acid                                          fenuron    N,N-dimethyl-N'-phenylurea                                          fenuron TCA                                                                               Salt of fenuron and TCA                                             flamprop   N-benzoyl-N-(3-chloro-4-fluorophenyl)-                                         DL-alanine                                                          fluazifop  (%)2-[4-[[5-(trifluoromethyl)-2-                                               pyridinyl]oxy]phenoxy]propanoic                                                acid                                                                fluazifop-P                                                                               (R)-2-[4-[[5-(trifluoromethyl)-2-                                              pryidinyl]oxy]phenoxy]propanoic                                                acid                                                                fluchloralin                                                                              N-(2-chloroethyl)-2,6-dinitro-N-propyl-                                        4-(trifluoromethyl)benzenamine                                      fluometuron                                                                               N,N-dimethyl-N'-[3-trifluoromethyl)                                            phenyl]urea                                                         fluoro-    3-chloro-4-(chloromethyl)-1-[3-                                     chloridone (trifluoromethyl)phenyl]-2-pyrroli-                                            dinone                                                              fluorodifen                                                                                -p-nitrophenyl a,a,a-trifluoro-2-nitro-                                        -p-tolyl ether                                                     fluorogly- carboxymethyl 5-[2-chloro-4-(tri-                                   cofen      fluoromethyl)phenoxy]-2-nitro-                                                 benzoate                                                            fluridone  1-methyl-3-phenyl-5-[3-(trifluoro-                                             methyl)phenyl]-4(1H)-pyridinone                                     fomesafen  5-[2-chloro-4-trifluoromethyl)phenoxy]-                                        N-(methylsulfonyl)-2-nitrobenzamide                                 fosamine   ethyl hydrogen (aminocarbonyl)phosphate                             glyphosate N-(phosphonomethyl)glycine                                          halozyfop  2-[4-[[3-chloro-5-(trifluoromethyl)-                                           2-pyridinyl]oxy]phenoxy]propanoic                                              acid                                                                hexaflurate                                                                               potassium hexafluoroarsenate                                        hexazinone 3-cyclohexyl-6-(dmethylamino)-1-methyl-                                        1,3,5-triazine-2,4(1H,3H)-dione                                     imazametha-                                                                               6-(4-isopropyl-4-methyl-5-oxo-2-                                    benz       imadazolin-2-yl)- .sub.-- m-toluic acid,                                       methyl ester                                                        imazapyr   (%)-[4,5-dihydro-4-methyl-4-(1-methyl-                                         ethyl)-5-oxo-1H-imidazol-2-yl]-3-                                              pyridinecarboxylic acid                                             imazaquin  2-[4,5-dihydro-4-methyl-4-(1-methyl-                                           ethyl)-5-oxo-1H-imidazol-2-yl]-3-                                              quinolinecarboxylic acid                                            imazethapyr                                                                               (%)-2-[4,5-dihydro-4-methyl-4-(1-methyl-                                       ethyl)-5-oxo-1H-imidazol-2-yl]-5-                                              ethyl-3-pyridinecarboxylic acid                                     ioxynil    4-hydroxy-3,5-diiodobenzonitrile                                    isopropalin                                                                               4-(1-methylethyl)-2,6-dinitro-N,N-                                             dipropylbenzenamine                                                 isoprotoron                                                                               N-(4-isopropylphenyl)-N',N'-dimethylurea                            isouron    N'-[(1,1-dimethylethyl)-3-isoxazolyl]-                                         N,N-dimethylurea                                                    isoxaben   N-[3-(1-ethyl-1-methylpropyl)-5-                                               isoxazolyl]-2,6-dimethoxybenzamide                                  karbutilate                                                                               3-[[(dimethylamino)carbonyl]amino]-                                            phenyl (1,1-dimethylethyl)-                                                    carbamate                                                           lactofen   (%)-2-ethoxy-1-methyl-2-oxoethyl 5-[2-                                         chloro-4-(trifluoromethyl)phenoxy]-                                            2-nitrobenzoate                                                     lenacil    3-cyclohexyl-6,7-dihydro-1H-cyclopenta-                                        pyrimidine-2,4(3H,5H)-dione                                         linuron    N'-(3,4-dichlorophenyl)-N-methoxy-N-                                           methylurea                                                          MAA        methylarsonic acid                                                  MAMA       monoammonium salt of MAA                                            MCPA       (4-chloro-2-methylphenoxy)acetic acid                               MCPB       4-(4-chloro-2-methylphenoxy)butanoic                                           acid                                                                mecoprop   (%)-2-(4-chloro-2-methylphenoxy)-                                              propanoic acid                                                      mefluidide N-[2,4-dimethyl-5-[[(trifluoromethyl)-                                         sulfonyl]amino]phenyl]acetamide                                     methal-    N-(2-methyl-2-propenyl)-2,6-dinitro-N-                              propalin   propyl-4-(trifluoromethyl)benzenamide                               methabenz- 1,3-dimethyl-3-(2-benzothiazolyl)urea                               thiazuron                                                                      metham     methylcarbamodithioic acid                                          methazole  2-(3,4-dichlorophenyl)-4-methyl-1,2,4-                                         oxadiazolidine-3,5-dione                                            methoxuron N'-(3-chloro-4-methoxyphenyl)N,N-                                              dimethylurea                                                        metolachlor                                                                               2-chloro-N-(2-ethyl-6-methylphenyl)-N-                                         (2-methoxy-1-methylethyl)acetamide                                  metribuzin 4-amino-6-(1,1-dimetylethyl)-3-(methyl-                                        thio)-1,2,4-triazin-5(4H)-one                                       metsulfuron                                                                               2-[[[[(4-methoxy-6-methyl-1,3,5-                                               triazin-2-yl)amino]carbonyl]amino]-                                            sulfonyl]benzoic acid, methyl ester                                 MH         1,2-dihydro-3,6-pyridazinedione                                     molinate   S-ethyl hexahydro-1H-azepine-1-carbo-                                          thioate                                                             monolinuron                                                                               3-( -p-chlorophenyl)-1-methoxy-1-methyl-                                       urea                                                                monuron    N'-(4-chlorophenyl)-N,N-dimethylurea                                monuron TCA                                                                               salt of monuron and TCA                                             MSMA       monosodium salt of MAA                                              napropamide                                                                               N,N-diethyl-2-(1-naphthalenyloxy)-                                             propanamide                                                         naptalam   2-[(1-naphthalenylamino)carbonyl]-                                             benzoic acid                                                        neburon    1-butyl-3-(3,4-dichlorphenyl)-1-methyl-                                        urea                                                                nitralin   4-(methylsulfonyl)-2,6-dinitro-N,N-                                            dipropylaniline                                                     nitrofen   2,4-dichloro-1-(4-nitrophenoxy)benzene                              nitrofluorfen                                                                             2-chloro-1-(4-nitrophenoxy)-4-(tri-                                            fluoromethyl)benzene                                                norea      N,N-dimethyl-N'-(octahydro-4,7-methano-                                        1H-inden-5-yl)urea 3aa,4a,5a,7a,7aa-                                           isomer                                                              norflurazon                                                                               4-chloro-5-(methylamino)-2-(3-(tri-                                            fluoromethyl)phenyl)-3(2H)-pyridaz-                                            inone                                                               oryzalin   4-(dipropylamino)-3,5-dinitrobenzene-                                          sulfonamide                                                         oxadiazon  3-[2,4-dichloro-5-(1-methylethoxy)-                                            phenyl]-5-(1,1-dimethylethyl-1,3,4-                                            oxadiazol-2-(3H)-one                                                oxyfluorfen                                                                               2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-                                        (trifluoromethyl)benzene                                            paraquat   1,1'-dimethyl-4,4'-dipyridinium ion                                 pebulate   S-propyl butylethylcarbamothioate                                   pendimethalin                                                                             N-(1-ethylpropyl)-3,4-dimethyl-2,6-                                            dinitrobenzenamine                                                  perfluidone                                                                               1,1,1-trifluoro-N-[2-methyl-4-(phenyl-                                         sulfonyl)phenyl]methanesulfonamide                                  phenmedipham                                                                              3-[(methoxycarbonyl)amino]phenyl-                                              (3-methylphenyl)carbamate                                           picloram   4-amino-3,5,6-trichloro-2-pyridine-                                            carboxylic acid                                                     PPG-1013   5-(2-chloro-4-(trifluoromethyl)phenoxy)-                                       2-nitroacetophenone oxime-O-acetic                                             acid, methyl ester                                                  procyazine 2-[[4-chloro-6-(cyclopropylamino)-1,3,5-                                       triazine-2-yl]amino]-2-methylpropane-                                          nitrile                                                             profluralin                                                                               N-(cyclopropylmethyl)-2,6-dinitro-N-                                           propyl-4-(trifluoromethyl)benzen-                                              amine                                                               prometon   6-methoxy-N,N'-bis(1-methylethyl)-                                             1,3,5-triazine-2,4-diamine                                          prometryn  N,N'-bis(1-methylethyl)-6-(methyl-                                             thio)-1,3,5-triazine-1,4-diamine                                    pronamide  3,5-dichloro N-(1,1-dimethyl-2-propyn-                                         yl)benzamide                                                        propachlor 2-chloro-N-(1-methylethyl-N-phenyl-                                            acetamide                                                           propanil   N-(3,4-dichlorophenyl)propanamide                                   propazine  6-chloro-N,N'-bis(1-methylethyl)-                                              1,3,5-triazine-2,4-diamine                                          propham    1-methylethyl phenylcarbamate                                       prosulfalin                                                                               N-[[4-(dipropylamino)-3,5-dinitro-                                             phenyl]sulfonyl]-S,S-dimethylsulfil-                                           imine                                                               prynachlor 2-chloro-N-(1-methyl-2-propynyl)acet-                                          anilide                                                             pyrazon    5-amino-3-chloro-2-phenyl-3(2H)-                                               pyridazinone                                                        quizalofop (%)-2-[4[(6-chloro-2-quinoxalinyl)]-                                           oxy]phenoxy]propanoic acid                                          secbumeton N-ethyl-6-methoxy-N'(1-methylpropyl)-                                          1,3,5-triazine-2,4-diamine                                          sethoxydim 2-[1-(ethoxyimino)butyl]-5-[2-(ethyl-                                          thio)propyl]-3-hydroxy-2-cyclohexene-                                          1-one                                                               siduron    N-(2-methylcyclohexyl)-N'-phenylurea                                simazine   6-chloro-N,N'-diethyl-1,3,5-triazine-                                          2,4-diamine                                                         sulfometuron                                                                              2-[[[[(4,6-dimethyl-2-pyrimidinyl)-                                            amino]carbonyl]amino]sulfonyl]-                                                benzoic acid, methyl ester                                          TCA        trichloroacetic acid                                                tebuthiuron                                                                               N-[5-(1,1-dimethylethyl)-1,3,4-thiadi-                                         azol-2-yl]-N,N'-dimethylurea                                        terbacil   5-chloro-3(1,1-dimethylethyl)-6-                                               methyl-2,4(1H,3H)-pyrimidinedione                                   terbuchlor N-(butoxymethyl)-2-chloro-N-[2-1,1-                                            dimethylethyl)-6-methylphenyl]-                                                acetamide                                                           terbuthyl- 2-(tert-butylamino)-4-chloro-6-ethyl-                               azine      amino)- .sub.- s-triazine                                           terbutol   2,6-di-tert-butyl- -p-tolyl methylcar-                                         bamate                                                              terbutryn  N-(1,1-dimethylethyl)-N'-ethyl-6-                                              methylthio)-2,3,5-triazine-2,4-                                     thiameturon                                                                               3-[[[[(4-methoxy-6-methyl-1,3,5-                                    methyl     triazin-2-yl)amino]carbonyl]amino]-                                            sulfonyl]2-thiophenecarboxylic acid,                                           methyl ester                                                        thiobencarb                                                                               S-[(4-chlorophenyl)methyl]diethylcar-                                          bamothioate                                                         triallate  S-(2,3,3-trichloro-2-propenyl)bis(1-                                           methylethyl)carbamothioate                                          triclopyr  [(3,5,6-trichloro-2-pyridinyl)-                                                oxy]acetic acid                                                     tridiphane 2-(3,5-dichlorophenyl)-2-(2,2,2-                                               trichloroethyl)oxirane                                              trifluralin                                                                               2,6-dinitro-N,N-dipropyl-4-(tri-                                               fluoromethyl)benzenamine                                            trimeturon 1-( -p-chlorophenyl)-2,3,3-trimethylpseu-                                      dourea                                                              2,4-       (2,4-dichlorophenoxy)acetic acid                                    2,4-B      4-(2,4-dichlorophenoxy)butanoic acid                                vernolate  S-propyl dipropylthiocarbamothioate                                 xylachlor  2-chloro-N-(2,3-dimethylphenyl-N-                                              (1-methylethyl)acetamide                                            ______________________________________                                    

Herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. Test procedures and results follow.

                  TABLE A                                                          ______________________________________                                         Biological Testing                                                             ______________________________________                                          ##STR52##              Compound 1                                              ##STR53##              Compound 2                                              ##STR54##              Compound 3                                              ##STR55##              Compound 4                                              ##STR56##              Compound 5                                              ##STR57##              Compound 6                                              ##STR58##              Compound 7                                              ##STR59##              Compound 8                                              ##STR60##              Compound 9                                              ##STR61##              Compound 10                                             ##STR62##              Compound 11                                             ##STR63##              Compound 12                                             ##STR64##              Compound 13                                            ______________________________________                                    

TEST A

Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galli), cheatgrass (Bromus secalinus), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria spp.), giant foxtail (Setaria faberi), morningglory (Ipomoea spp.), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), and wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in height from two to eighteen cm (two to three leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for approximately sixteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table A, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result. The accompanying descriptive symbols have the following meanings:

B=burn injury;

C=chlorosis/necrosis;

E=inhibition of emergence;

G=growth retardation;

H=formative effect;

P=terminal bud injury; and

S=albinism.

                                      TABLE A                                      __________________________________________________________________________     POSTEMERGENCE                                                                          Cmpd 1                                                                               Cmpd 2 Cmpd 3                                                                              Cmpd 4 Cmpd 5 Cmpd 6 Cmpd 7                          RATE (g/ha)                                                                            400                                                                               100                                                                               400 100                                                                               100  400 100                                                                               400 50 400 100                                                                               400 100                         __________________________________________________________________________     Barley  0  0  0   0  0    0   0  0   0  0   0  0   0                           Barnyardgrass                                                                          9H 0  5H  0  9H   5C,9H                                                                              4H 9C  2H 5H  0  3H  0                           Cheatgrass                                                                             2G 0  0   0  0    0   0  2G  0  0   0  0   0                           Cocklebur                                                                              2H 0  1C  1C 1H   3C,5H                                                                              2C 2C,4H                                                                              2C 2C  1C 1C,3G                                                                              0                           Corn    2G 0  0   0  2G   2C,6G                                                                              0  2C,2G                                                                              0  0   0  0   0                           Cotton  0  0  0   0  0    0   0  7H  0  6H  0  0   0                           Crabgrass                                                                              8H 5G 2S,5G                                                                              0  0    9H  4H 9H  8H 0   0  7H  0                           Giant foxtail                                                                          9H 5H 3G  0  8H   9H  9H 9H  7H 0   0  3G  0                           Morningglory                                                                           0  0  0   0  2C   0   0  0   0  0   0  0   0                           Nutsedge                                                                               0  0  0   0  3G   0   0  2C,3G                                                                              0  0   0  0   0                           Rice    3G 0  0   0  0    0   0  0   0  1C  0  0   0                           Sorghum 2G 0  0   0  0    3G  0  0   0  0   0  0   0                           Soybean 2H 0  0   0  2H   0   0  4H  0  1C,7G                                                                              0  0   0                           Sugar beet                                                                             7G 0  0   0  0    0   0  0   0  0   0  0   0                           Velvetleaf                                                                             5G 5G 1C,4G                                                                              3G 1C,3G                                                                               4H  0  6H  0  4G  2G 0   0                           Wheat   2G 0  0   0  2G   0   0  0   0  0   0  0   0                           Wild oat                                                                               5G 0  0   0  0    0   0  0   0  0   0  0   0                           __________________________________________________________________________             Cmpd 8  Cmpd 9  Cmpd 10 Cmpd 11 Cmpd 12 Cmpd 13                        RATE (g/ha)                                                                            400 100 400 100 400 100 400 100 400 100 400 100                        __________________________________________________________________________     Barley  0   0   8H  2G  8G  0   0   0   0   0   0   0                          Barnyardgrass                                                                          9C  3C,9H                                                                              9C  9C  9C  4C,9G                                                                              3C,9H                                                                              8H  0   0   1H  0                          Cheatgrass                                                                             2G  0   9H  2G  9G  1C  3G  2G  0   0   0   0                          Cocklebur                                                                              2C  1C  2C,6H                                                                              2C  2C,5H                                                                              1C,2H                                                                              3C  2C  1C  0   --  0                          Corn    0   0   3C,7H                                                                              3C,5H                                                                              3C,8H                                                                              5H  2G  0   0   0   0   0                          Cotton  8H  0   3H  3H  10P,8G                                                                             0   2C  0   0   0   0   0                          Crabgrass                                                                              9H  9H  9H  9H  9H  9H  9G  9G  0   0   0   0                          Giant foxtail                                                                          4C,9H                                                                              3C,9H                                                                              5C,9H                                                                              9H  4C,9G                                                                              4C,9G                                                                              9G  2G  2G  0   3G  0                          Morningglory                                                                           0   0   1H  0   1H  0   0   0   0   0   0   0                          Nutsedge                                                                               0   0   3C,9H                                                                              0   --  0   --  0   0   0   0   0                          Rice    0   0   9C  2G  8G  0   0   0   0   0   0   0                          Sorghum 0   0   5H  3H  8H  0   0   0   0   0   0   0                          Soybean 1C,3H                                                                              1H  6C,9H                                                                              6H  6H  0   1C  0   0   0   0   0                          Sugar beet                                                                             5H  2H  5C,9H                                                                              0   6H  1H  0   0   0   0   0   0                          Velvetleaf                                                                             3C,7H                                                                              1H  3C,9H                                                                              6H  8H  7H  2C,6H                                                                              2C,3H                                                                              0   0   0   0                          Wheat   0   0   9G  2G  2G  0   0   0   0   0   0   0                          Wild oat                                                                               0   0   9H  4G  5H  2G  0   0   0   0   0   0                          __________________________________________________________________________     PREEMERGENCE                                                                           Cmpd 1                                                                               Cmpd 2  Cmpd 3                                                                              Cmpd 4  Cmpd 5 Cmpd 6                                                                               Cmpd 7                         RATE (g/ha)                                                                            400                                                                               100                                                                               400 100 100  400 100 400 50 400                                                                               100                                                                               400 100                        __________________________________________________________________________     Barley  0  0  0   0   0    7H  0   0   0  0  0  0   0                          Barnyardgrass                                                                          10H                                                                               10H                                                                               10H 10H 10H  10H 10H 10H 10H                                                                               10H                                                                               8H 10H 7H                         Cheatgrass                                                                             9E 7G 4G  0   3G   2G  0   3G  2G 2G 0  4G  0                          Cocklebur                                                                              0  0  1C  0   2G   0   0   3H  -- 5G 0  0   0                          Corn    9H 2G 2G  0   2G   3C,6H                                                                              4H  5C,8H                                                                              0  3G 0  0   0                          Cotton  0  0  0   0   0    0   0   0   0  0  0  0   0                          Crabgrass                                                                              10H                                                                               10H                                                                               9H  6G  4C,9H                                                                               9H  9H  10H 10H                                                                               2G 0  9H  5G                         Giant foxtail                                                                          10H                                                                               10H                                                                               9H  8G  9H   10H 5C,9H                                                                              10H 10H                                                                               9H 3G 9H  7G                         Morningglory                                                                           0  0  0   0   0    0   0   0   0  2H 0  0   0                          Nutsedge                                                                               10E                                                                               0  0   0   0    0   0   0   0  0  0  0   0                          Rice    5G 0  0   0   0    0   0   3G  0  0  0  0   0                          Sorghum 10H                                                                               9H 2C,6G                                                                              0   8H   3C,9H                                                                              6H  3C,7H                                                                              2G 5G 0  0   0                          Soybean 0  0  0   0   0    2G  0   0   0  0  0  0   0                          Sugar beet                                                                             5H 0  4G  0   0    0   0   0   0  0  0  0   0                          Velvetleaf                                                                             6H 2H 7G  4G  8H   7H  4H  8H  3H 7H 0  3C,5H                                                                              1H                         Wheat   0  0  0   0   3G   0   0   5H  0  0  0  0   0                          Wild oat                                                                               6G 0  3C,7H                                                                              2C,5G                                                                              0    9H  2G  7H  0  0  0  2C  0                          __________________________________________________________________________             Cmpd 8  Cmpd 9  Cmpd 10 Cmpd 11                                                                               Cmpd 12 Cmpd 13                         RATE (g/ha)                                                                            400 100 400 100 400 100 400 100                                                                               400 100 400 100                         __________________________________________________________________________     Barley  0   0   8H  0   8H  0   3G  0  0   0   0   0                           Barnyardgrass                                                                          10H 10H 10H 10H 10H 10H 10H 9H 0   0   2C,8G                                                                              2C,5G                       Cheatgrass                                                                             0   0   9H  6H  9H  9G  6G  5G 0   0   0   0                           Cocklebur                                                                              0   0   0   0   5G  0   1C,2H                                                                              0  0   0   0   0                           Corn    0   0   4C,8H                                                                              4G  10H 3C,8H                                                                              4C,8H                                                                              3G 0   0   0   0                           Cotton  0   0   8H  0   0   0   2G  0  0   0   0   0                           Crabgrass                                                                              10H 9H  10H 10H 10H 10H 10H 8H 3G  0   5G  0                           Giant foxtail                                                                          10H 10H 10H 10H 10H 10H 10H 8H 4G  0   3G  0                           Morningglory                                                                           0   0   0   0   0   0   0   0  0   0   0   0                           Nutsedge                                                                               0   0   3C,9G                                                                              5G  2C,8G                                                                              10E 0   0  0   0   10E 0                           Rice    0   0   3G  2G  8H  0   2C,2G                                                                              0  0   0   0   0                           Sorghum 3C,8H                                                                              0   9H  9H  10H 3C,9H                                                                              4C,8G                                                                              4G 0   0   2G  0                           Soybean 0   0   9H  8H  4H  0   0   0  0   0   0   0                           Sugar beet                                                                             3H  2H  3H  2H  4H  2H  0   0  0   0   2G  0                           Velvetleaf                                                                             8H  6H  4C,9H                                                                              8H  5H  2C,6H                                                                              5H  2H 0   0   4H  0                           Wheat   0   0   7G  3G  2C,5G                                                                              0   2G  0  0   0   0   0                           Wild oat                                                                               0   0   8H  2G  9H  2G  2C,8H                                                                              2H 0   0   0   0                           __________________________________________________________________________

TEST B

Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galli), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria spp.), downy brome (Bromus tectorum), giant foxtail (Setaria faberi), green foxtail (Setaria viridis), jimsonweed (Datura stramonium), johnsongrass (Sorghum halepense), lambsquarters (Chenopodium album), morningglory (Ipomoea spp.), rape (Brassica napus), rice (Oryza sativa), sicklepod (Cassia obtusifolia), soybean (Glycine max), sugar beet (Beta vulgaris), teaweed (Sida spinosa), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in height from two to eighteen cm (two to three leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for approximately 24 days, after which all species were compared to controls and visually evaluated. Preemergence and postemergence application rates for each compound are listed in Table B. Plant response ratings, summarized in Table B, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

                                      TABLE B                                      __________________________________________________________________________     POSTEMERGENCE                                                                            Cmpd 1                                                                               Cmpd 2       Cmpd 4        Cmpd 5                              RATE (g/ha)                                                                              500                                                                               250                                                                               250 125                                                                               62 31 250 125                                                                               62  31 250 125                                                                               62  31                       __________________________________________________________________________     Barley    0  0  0   0  0  0  30  0  0   0  0   0  0   0                        Barnyardgrass                                                                            85 80 90  90 90 50 70  65 60  40 60  50 30  0                        Blackgrass                                                                               30 20 0   0  0  0  100 90 70  40 30  0  0   0                        Chickweed 0  0  0   0  0  0  0   0  0   0  0   0  0   0                        Cocklebur 0  0  0   0  0  0  30  0  0   0  0   0  0   0                        Corn      20 0  30  20 0  0  0   0  0   0  0   0  0   0                        Cotton    0  0  0   0  0  0  0   0  0   0  0   0  0   0                        Crabgrass 90 50 70  20 0  0  90  80 70  60 70  -- 30  0                        Downy brome                                                                              0  0  0   0  0  0  0   0  0   0  0   0  0   0                        Giant foxtail                                                                            90 90 40  30 0  0  90  60 30  0  90  80 60  30                       Green foxtail                                                                            40 30 40  20 0  0  70  60 40  30 60  0  0   0                        Jimsonweed                                                                               0  0  0   0  0  0  50  30 0   0  30  0  0   0                        Johnsongrass                                                                             30 20 0   0  0  0  0   0  0   0  30  0  0   0                        Lambsquarters                                                                            40 30 80  20 0  0  80  70 60  30 90  60 30  0                        Morningglory                                                                             0  0  0   0  0  0  50  0  0   0  0   0  0   0                        Nutsedge  60 0  0   0  0  0  --  -- --  -- --  -- --  --                       Rape      0  0  30  20 0  0  80  50 0   0  0   0  0   0                        Rice      0  0  0   0  0  0  0   0  0   0  70  20 0   0                        Sicklepod 0  0  0   0  0  0  30  0  0   0  30  0  0   0                        Soybean   0  0  0   0  0  0  0   0  0   0  0   0  0   0                        Sugar beet                                                                               60 20 0   0  0  0  0   0  0   0  30  0  0   0                        Teaweed   0  0  0   0  0  0  0   0  0   0  0   0  0   0                        Velvetleaf                                                                               60 40 40  20 0  0  70  30 30  0  30  30 0   0                        Wheat     0  0  0   0  0  0  0   0  0   0  0   0  0   0                        Wild buckwheat                                                                           0  0  0   0  0  0  30  0  0   0  0   0  0   0                        Wild oat  30 20 0   0  0  0  0   0  0   0  0   0  0   0                        __________________________________________________________________________     PREEMERGENCE                                                                             Cmpd 1      Cmpd 2      Cmpd 4      Cmpd 5                           RATE (g/ha)                                                                              500                                                                               250                                                                               125                                                                               62 250                                                                               125                                                                               62 31 250                                                                               125                                                                               62 31 250                                                                               125                                                                               62 31                      __________________________________________________________________________     Barley    0  0  0  0  0  0  0  0  50 30 0  0  0  0  0  0                       Barnyardgrass                                                                            100                                                                               100                                                                               100                                                                               30 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                     Blackgrass                                                                               100                                                                               100                                                                               70 40 40 30 30 30 100                                                                               100                                                                               60 60 100                                                                               100                                                                               100                                                                               85                      Chickweed 0  0  0  0  0  0  0  0  70 70 30 0  30 20 0  0                       Cocklebur 20 0  0  0  0  -- 0  0  100                                                                               0  0  -- 50 0  -- --                      Corn      30 20 20 0  0  0  0  0  100                                                                               80 50 20 70 50 0  0                       Cotton    0  0  0  0  0  0  0  0  30 30 0  0  30 20 0  --                      Crabgrass 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               90 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                     Downy brome                                                                              90 90 90 30 0  0  0  0  100                                                                               100                                                                               40 20 60 40 0  0                       Giant foxtail                                                                            100                                                                               100                                                                               100                                                                               50 100                                                                               100                                                                               80 70 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                     Green foxtail                                                                            100                                                                               100                                                                               100                                                                               100                                                                               90 80 70 30 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                     Jimsonweed                                                                               0  0  0  0  0  0  0  0  80 40 30 0  0  0  0  0                       Johnsongrass                                                                             80 70 70 40 50 30 20 20 100                                                                               80 75 40 100                                                                               100                                                                               100                                                                               100                     Lambsquarters                                                                            80 80 -- 70 90 80 50 50 0  0  0  0  80 60 50 30                      Morningglory                                                                             0  0  0  0  0  0  0  0  0  0  0  0  0  0  0  0                       Nutsedge  30 0  0  0  0  0  0  0  20 0  0  0  -- -- -- --                      Rape      20 0  0  0  0  0  0  0  40 0  0  0  0  0  0  0                       Rice      40 10 0  0  30 0  0  0  40 0  0  0  0  0  0  0                       Sicklepod 0  0  0  0  100                                                                               40 0  0  50 30 0  0  50 30 0  0                       Soybean   0  0  0  0  0  0  0  0  0  0  0  0  20 0  0  0                       Sugar beet                                                                               30 20 0  0  0  0  0  0  -- 50 30 30 50 30 0  0                       Teaweed   50 40 30 20 60 60 60 0  80 -- 70 0  70 30 0  0                       Velvetleaf                                                                               80 70 40 20 70 50 20 0  90 80 50 0  100                                                                               100                                                                               80 30                      Wheat     0  0  0  0  0  0  0  0  30 0  0  0  0  0  0  0                       Wild buckwheat                                                                           90 60 40 30 0  0  0  0  0  0  0  0  0  0  0  0                       Wild oat  100                                                                               60 40 30 0  0  0  0  40 30 30 0  40 30 20 0                       __________________________________________________________________________

TEST C

Plastic pots were partially filled with silt loam soil. The soil was then saturated with water. Indica and Japonica rice (Oryza sativa) seedlings at the 2.0 to 2.5 leaf stage, seeds of barnyardgrass (Echinochloa crus-galli), bulrush (Scirpus mucronatus), and umbrella sedge (Cyperus difformis), and sprouted tubers of arrowhead (Sagittaria spp). and waterchestnut (Eleocharis spp.) were planted into this soil. Several days after planting, water levels were raised to 3 cm above the soil surface and maintained at this level throughout the test. Chemical treatments were formulated in a non-phytotoxic solvent and applied directly to the paddy water. Treated plants and controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table C, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

                                      TABLE C                                      __________________________________________________________________________             Cmpd 1         Cmpd 2         Cmpd 3                                   RATE (g/ha)                                                                            1000                                                                              500                                                                               250                                                                               125                                                                               64 1000                                                                              500                                                                               250                                                                               125                                                                               64 500                                                                               250                                                                               125                                                                               64 32                           __________________________________________________________________________     Arrowhead                                                                              70 90 70 60 30 0  0  0  0  0  -- -- -- -- --                           Barnyardgrass                                                                          100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               95 95                           Bulrush 95 95 95 90 0  90 90 0  0  0  90 90 90 90 90                           Rice (Indica)                                                                          50 20 0  0  0  30 30 0  0  0  80 80 40 30 0                            Rice (Japonica)                                                                        30 20 0  0  0  20 0  0  0  0  90 80 50 20 0                            Umbrella sedge                                                                         100                                                                               100                                                                               100                                                                               100                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               0  100                                                                               100                                                                               100                                                                               100                                                                               100                          Waterchestnut                                                                          100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               70 100                                                                               0  0  90 60 50 70 40                           __________________________________________________________________________             Cmpd 5         Cmpd 7         Cmpd 10                                  Rate (g/ha)                                                                            500                                                                               250                                                                               125                                                                               64 32 500                                                                               250                                                                                125                                                                              64 32 500                                                                               250                                                                               125                                                                               64 32                           __________________________________________________________________________     Arrowhead                                                                              90 0  0  0  0  0  0  0  0  0  95 95 60 95 0                            Barnyardgrass                                                                          100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               70 100                                                                               100                                                                               100                                                                               100                                                                               100                          Bulrush 95 95 95 95 80 95 0  0  0  0  95 95 90 60 0                            Rice (Indica)                                                                          50 30 20 0  0  0  0  0  0  0  60 40 0  0  0                            Rice (Japonica)                                                                        40 30 0  0  0  0  0  0  0  0  70 50 0  0  0                            Umbrella sedge                                                                         100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               100                          Waterchestnut                                                                          95 0  0  0  0  0  0  0  0  0  95 95 95 0  0                            __________________________________________________________________________

TEST D

Seeds of spring and winter barley (Hordeum vulgare), black nightshade (Solanum nigrum), blackgrass (Alopercurus myosuroides), bluegrass (Poa annua), catchweed bedstraw (Gallium aparine), cheatgrass (Bromus secalinus), downy brome (Bromus tectorum), field pennycress (Thlaspi arvense), field violet (Viola arvensis), green foxtail (Setaria viridis), Italian ryegrass (Lolium multiflorum), ivyleaf speedwell (Veronica hederaefolia), jointed goatgrass (Aegilops cylindrica), kochia (Kochia scoparia), lambsquarters (Chenopodium album), Persian speedwell (Veronica persica), rape (Brassica napus), Russian thistle (Salsola kali), scentless chamomile (Matricaria inodora), sugar beet (Beta vulgaris), spring and winter wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua) were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. Postemergence applications of test chemicals were also applied to these same crop and weed species. Plants ranged in height from two to twenty-four cm (two to three leaf stage) for postemergence treatments. Blackgrass and wild oat were treated postemergence at two growth stages--the first stage being at two to three leaves and the second stage being approximately at four leaves or in the initial stages of tillering. Treated plants and controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Rates of application of each compound are listed in Table D. Plant response ratings, summarized in Table D, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control.

                                      TABLE D                                      __________________________________________________________________________                Cmpd 1       Cmpd 2                                                 RATE (g/ha)                                                                               500                                                                               250                                                                               125                                                                               64  500                                                                               250                                                                               125                                                                               64                                            __________________________________________________________________________     POSTEMERGENCE                                                                  Barley (Spring)                                                                           0  0  0  0   0  0  0  0                                             Barley (Winter)                                                                           0  0  0  0   0  0  0  0                                             Black nightshade                                                                          10 0  0  0   10 0  0  0                                             Blackgrass 10 0  0  0   20 0  0  0                                             Blackgrass (Stage 2)                                                                      0  0  0  0   0  0  0  0                                             Bluegrass  50 50 20 0   20 0  0  0                                             Catchweed bedstraw                                                                        0  0  0  0   20 10 0  0                                             Cheatgrass 0  0  0  0   0  0  0  0                                             Downy brome                                                                               0  0  0  0   0  0  0  0                                             Field pennycress                                                                          10 0  0  0   10 0  0  0                                             Field violet                                                                              0  0  0  0   0  0  0  0                                             Green foxtail                                                                             60 60 0  0   20 0  0  0                                             Italian ryegrass                                                                          0  0  0  0   0  0  0  0                                             Ivyleaf speedwell                                                                         0  0  0  0   0  0  0  0                                             Jointed goatgrass                                                                         0  0  0  0   0  0  0  0                                             Kochia     0  0  0  0   20 0  0  0                                             Lambsquarters                                                                             10 0  0  0   10 0  0  0                                             Persian speedwell                                                                         0  0  0  0   0  0  0  0                                             Rape       50 10 0  0   10 0  0  0                                             Russian thistle                                                                           0  0  0  0   0  0  0  0                                             Scentless chamomile                                                                       0  0  0  0   0  0  0  0                                             Sugar beet 10 0  0  0   20 0  0  0                                             Wheat (Spring)                                                                            0  0  0  0   0  0  0  0                                             Wheat (Winter)                                                                            0  0  0  0   0  0  0  0                                             Wild buckwheat                                                                            0  0  0  0   0  0  0  0                                             Wild oat   0  0  0  0   0  0  0  0                                             Wild oat (Stage 2)                                                                        0  0  0  0   0  0  0  0                                             PREEMERGENCE                                                                   Barley (Spring)                                                                           20 10 0  0   0  0  0  0                                             Barley (Winter)                                                                           20 0  0  0   0  0  0  0                                             Black nightshade                                                                          0  0  0  0   0  0  0  0                                             Blackgrass 100                                                                               100                                                                               20 0   90 30 10 10                                            Blackgrass (Stage 2)                                                           Bluegrass  100                                                                               100                                                                               50 10  100                                                                               90 60 50                                            Catchweed bedstraw                                                                        20 0  0  0   0  0  0  0                                             Cheatgrass 70 20 0  0   10 0  0  0                                             Downy brome                                                                               90 60 50 10  70 20 0  0                                             Field pennycress                                                                          30 0  0  0   60 50 20 0                                             Field violet                                                                              40 20 20 0   100                                                                               70 20 0                                             Green foxtail                                                                             100                                                                               100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                           Italian ryegrass                                                                          90 80 20 20  80 60 20 0                                             Ivyleaf speedwell                                                                         60 0  0  0   50 10 0  0                                             Jointed goatgrass                                                                         20 10 0  0   10 0  0  0                                             Kochia     100                                                                               80 40 20  30 20 0  0                                             Lambsquarters                                                                             60 60 50 40  50 50 20 0                                             Persian speedwell                                                                         20 20 0  0   10 0  0  0                                             Rape       50 10 0  0   80 70 60 30                                            Russian thistle                                                                           20 0  0  0   10 0  0  0                                             Scentless chamomile                                                                       40 40 10 10  0  0  0  0                                             Sugar beet 70 40 40 20  70 50 30 30                                            Wheat (Spring)                                                                            10 0  0  0   0  0  0  0                                             Wheat (Winter)                                                                            20 10 0  0   0  0  0  0                                             Wild buckwheat                                                                            10 0  0  0   0  0  0  0                                             Wild oat   30 0  0  0   10 10 0  0                                             __________________________________________________________________________ 

What is claimed is:
 1. A compound of Formula I ##STR65## wherein: X is (CH₂)_(m) ;Z is (CR₃ R₄)_(n) ; m is 1; n is 2; R₁ is H or a straight-chain C₁ -C₃ alkyl; R₂ is H, C₁ -C₆ alkyl, C₂ -C₄ alkenyl, C₂ -C₄ alkynyl, phenyl or C₁ -C₄ alkyl substituted by halogen, Ph, OH, CN, OR_(a), SO₂ R_(a), PhSO₂, N₃, CO₂ R_(a), or CO₂ H; R₃ is H or C₁ -C₃ alkyl; R₄ is H or CH₃ ; R₃ and R₄ can be taken together to form a 5- or 6-membered carbocyclic ring; W is ##STR66## R₅ is H, halogen, R_(a), OR_(a), SR_(a) or CN; R₆ is H, F, Cl, CH₃, OCH₃, OH or OR_(a) ; and R_(a) is C₁ -C₃ alkyl.
 2. A compound of claim 1 wherein:R₂ is C₁ -C₃ alkyl, C₂ -C₃ alkenyl, C₂ -C₃ alkynyl, or C₁ -C₂ alkyl substituted by OH, CN, OCH₃, SO₂ CH₃, SO₂ Ph or CO₂ CH₃ ; and R₅ is H, F, Cl, Br, CH₃, OCH₃, SCH₃ or CN.
 3. A compound of claim 2 wherein:R₃ is H or CH₃.
 4. The compound of claim 3 which is:7-oxabicyclo((2.2.1))heptane'2-(2,3-dihydro-1H-inden-1-yloxy)-1-methyl-4-(1-methylethyl)--.
 5. The compound of claim 3 which is:2-(2,3-dihydro-1H-inden-1-yloxy)-1,4-diethyl-7-oxabicyclo[2.2.1]heptane.
 6. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of any one of claims 1, 2, 3, 4 and 5 and at least one of the following: surfactant, solid or liquid diluent.
 7. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of any one of claims 1, 2, 3, 4 and
 5. 8. The method of claim 7 wherein the undesired vegetation is present in rice.
 9. A method for controlling the growth of undesired vegetation in rice which comprises applying to the locus to be protected an effective amount of said composition of claim
 6. 